(2-Amino-5-'XH'phenyl)(2-'XH'phenyl)methanone by Asch

Reaxys

PubChem

eMolecules

Reactions (329)

Yield

Substances (27)

Citations (284)

Conditions

References

199

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Multi-step reaction with 3 steps 1.1: sec.-butyllithium / tetrahydrofuran; cyclohexane / 0.42 h / -78 °C 1.2: -25 - 20 °C 2.1: sodium acetate; pyridinium chlorochromate / dichloromethane / 2.5 h / 20 °C 3.1: sodium hydroxide / ethanol; water / 31 h / |Reflux View Scheme

200

Rx-ID: 44430153 Find similar reactions

ANVYL, LLC; DASSE, Olivier

Patent: WO2016/154039 A1, 2016 ; Title/Abstract Full Text Show Details

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Rx-ID: 44430163 Find similar reactions

ANVYL, LLC; DASSE, Olivier

Patent: WO2016/154039 A1, 2016 ; Title/Abstract Full Text Show Details

201

Synthesize Find similar 610 mg

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With sodium hydroxide in ethanol; water

31 h; Reflux; Hide Experimental Procedure

Rx-ID: 44430165 Find similar reactions

ANVYL, LLC; DASSE, Olivier

Patent: WO2016/154039 A1, 2016 ; Location in patent: Paragraph 00156 ; Title/Abstract Full Text Show Details

2:00156] Synthesis of (2-amino-5-chlorophenyl)(phenyl-d5)methanone:

A solution of tert-butyl (2-(benzoyl-2,3,4,5,6-d5)-4-chlorophenyl)carbamate (1.05 g, 3.12 mmol) in EtOH (17 mL) was treated with a 10percent NaOH (2.5 M; 3.4 mL) aqueous solution added dropwise. The mixture was then refluxed for 24 hours. An additional 3 mL of 2.5 N NaOH was added and the reaction mixture was refluxed for an additional 7 hours. After cooling to room temperature, the organic solvent removed in vacuo. The residue was diluted with ice-water. It was extracted with 75 mL of EtOAc. The phases were separated. The aqueous layer was extracted with EtOAc (2 x 40 mL). The combined organic layers were washed with water (50 mL, brine added to separate phases) and brine. After drying (MgS04), the mixture was filtered and concentrated in vacuo. To yield a red-orange oil that solidified on standing (730 mg). The crude reaction mixture was purified by flash silica gel chromatography eluting with 100percent CH2CI2. The product was obtained as a yellow-orange solid (610 mgs, 2.58mmols). MS: (M+H) 237 A

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202

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Rx-ID: 3809808 Find similar reactions

A: 24% B: 4% C: 6% D: 8%

With manganese triacetate in water; acetic acid

T=100°C; 0.1 h; Further byproducts given;

Nishino; Kurosawa

Bulletin of the Chemical Society of Japan, 1983 , vol. 56, # 6 p. 1682 - 1687 Title/Abstract Full Text View citing articles Show Details

203

Synthesize Find similar Rx-ID: 3809812 Find similar reactions

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A: 6% B: 4% C: 65% D: 6%

With manganese triacetate in acetic acid

0.2 h; Heating;

Nishino; Kurosawa

Bulletin of the Chemical Society of Japan, 1983 , vol. 56, # 6 p. 1682 - 1687 Title/Abstract Full Text View citing articles Show Details

A: 7% B: 5% C: 44% D: 31%

With manganese triacetate in acetic acid

0.0833333 h; Heating;

Nishino; Kurosawa

Bulletin of the Chemical Society of Japan, 1983 , vol. 56, # 6 p. 1682 - 1687 Title/Abstract Full Text View citing articles Show Details

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204

Synthesize Find similar Rx-ID: 3809813 Find similar reactions

A: 4% B: 3% C: 10% D: 30%

With manganese triacetate in acetic acid

T=100°C; 0.116667 h; Further byproducts given;

Nishino; Kurosawa

Bulletin of the Chemical Society of Japan, 1983 , vol. 56, # 6 p. 1682 - 1687 Title/Abstract Full Text View citing articles Show Details

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205

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Rx-ID: 3577563 Find similar reactions

A: 7% B: 34% C: 2% D: 17%

With manganese triacetate in acetic acid

T=100°C; 0.366667 h;

Nishino; Kurosawa

Bulletin of the Chemical Society of Japan, 1983 , vol. 56, # 6 p. 1682 - 1687 Title/Abstract Full Text View citing articles Show Details

A: 7% B: 34% C: 2% D: 17%

With manganese triacetate in acetic acid

T=100°C; 0.366667 h;

Nishino; Kurosawa

Bulletin of the Chemical Society of Japan, 1983 , vol. 56, # 6 p. 1682 - 1687 Title/Abstract Full Text View citing articles Show Details

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206

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With sulfuric acid; water; acetic acid in dichloromethane

8 h; Heating; Yield given. Yields of byproduct given;

Bubner; Kasbohm; Heise; Richter

Pharmazie, 1995 , vol. 50, # 1 p. 71 - 72 Title/Abstract Full Text View citing articles Show Details

With sulfuric acid; water; acetic acid in dichloromethane

8 h; Heating; Yield given. Yields of byproduct given;

Bubner; Kasbohm; Heise; Richter

Pharmazie, 1995 , vol. 50, # 1 p. 71 - 72 Title/Abstract Full Text View citing articles Show Details

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207

Synthesize Find similar Rx-ID: 3729583 Find similar reactions

With hydrogenchloride

multistep reaction: acid hydrolysis, photolysis;

Schutz; Fitz

Arzneimittel-Forschung/Drug Research, 1982 , vol. 32, # 3 p. 177 - 183 Title/Abstract Full Text View citing articles Show Details

208

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With hydrogenchloride

multistep reaction: acid hydrolysis, photolysis;

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Schutz; Fitz

Arzneimittel-Forschung/Drug Research, 1982 , vol. 32, # 3 p. 177 - 183 Title/Abstract Full Text View citing articles Show Details

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209

Synthesize Find similar Rx-ID: 3778711 Find similar reactions

With hydrogenchloride

multistep reaction: acid hydrolysis, photolysis;

Schutz; Fitz

Arzneimittel-Forschung/Drug Research, 1982 , vol. 32, # 3 p. 177 - 183 Title/Abstract Full Text View citing articles Show Details

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210

Synthesize Find similar Rx-ID: 3087546 Find similar reactions

With potassium hydroxide

5 h; Heatinghydrolysis;

Schleuder; Patow; Richter

Pharmazie, 1983 , vol. 38, # 12 p. 882 - 883 Title/Abstract Full Text View citing articles Show Details

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211

Synthesize Find similar Rx-ID: 3471887 Find similar reactions

With potassium hydroxide

5 h; Heatinghydrolysis;

Schleuder; Patow; Richter

Pharmazie, 1983 , vol. 38, # 12 p. 882 - 883 Title/Abstract Full Text View citing articles Show Details

212

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94%

Hide Experimental Procedure

Rx-ID: 5972145 Find similar reactions

Teijin Limited

Patent: US4169150 A1, 1979 ; Title/Abstract Full Text Show Details

8:EXAMPLE 8 [PREPARATION OF COMPOUND (II)]

EXAMPLE 8 [PREPARATION OF COMPOUND (II)] In the same way as in Example 7 except that 2-amino-5-chloro-2'-fluorobenzophenone was used instead of 2-amino-2',5-dichlorobenzopnenone were obtained light yellow crystals having melting point 150°-152° C. in 94percent yield. Recrystallization from methylene chloride-n-hexane afforded light yellow prisms having melting point 152°-153° C. The spectral data and the result of elemental analysis of the product were as follows: IR (KBr) cm-1: 1764, 1709, 1662, 1608, 1480, 1417, 1393 NMR (CDCl3) from TMS, δ (ppm): 1.68 (3H, s, CH3) 1.76 (3H, s, CH3) νA 4.57 and νB 4.32 (2H, ABq, J=15.5 Hz, CH2 N) 5.76 (1H, s, H on the pyrrole ring) 6.86-7.80 (11H, m, H on the benzene rings) Anal. Calcd. for C28 H20 ClFN2 O3: C, 69.07; H, 4.14; N, 5.75; Found: C, 68.83; H, 4.01; N, 5.72.

o-Fluorbenzoylchlorid, p-Chloranilin;

Hoffmann-La Roche

Patent: CH414652 , 1959 ; Chem.Abstr., 1968 , vol. 68, # 69054s Full Text Show Details

F.Hoffmann La Roche and Co AG

Patent: CH414652US3427304 , 1966 ; Full Text Show Details

o-FC6H4COCl, p-ClC6H4NH2, ZnCl2;

Hide Details

Hoffmann-La Roche

Patent: US3123529 , 1962 ; Chem.Abstr., 1964 , vol. 60, # 12035 Full Text Show Details

aus Benzodiazepinon (III) durch saure Hydrolyse;

de Silva; Strojny

Journal of pharmaceutical sciences, 1971 , vol. 60, # 9 p. 1303 - 1314 Title/Abstract Full Text View citing articles Show Details

aus Benzodiazepinon (IV) durch saure Hydrolyse;

de Silva; Strojny

Journal of pharmaceutical sciences, 1971 , vol. 60, # 9 p. 1303 - 1314 Title/Abstract Full Text View citing articles Show Details

2-Fluor-benzoylchlorid 1) Erhitzen mit 4-Chlor-anilin u. ZnCl2 2) sd. wss. HCl 3) sd. wss. H2SO4;

Sternbach et al.

Journal of Organic Chemistry, 1962 , vol. 27, p. 3781,3782, 3786 Full Text View citing articles Show Details

2-Fluor-benzoylchlorid, 1) 4-Chlor-anilin, ZnCl2, 2) H2SO4;

Hoffmann-La Roche

Patent: DE1136709 , 1962 ; Chem.Abstr., 1963 , vol. 59, # 12827 Full Text Show Details

2-Fluor-benzoylchlorid, 4-Chloranilin, ZnCl2;

Reeder; Sternbach

Patent: US3136815 , 1960 ; Chem.Abstr., 1964 , vol. 61, # 9515f Full Text Show Details

4-Chlor-anilin, 2-Fluor-benzoylchlorid, ZnCl2;

Reeder; Sternbach

Patent: US3141890 , 1962 ; Chem.Abstr., 1964 , vol. 61, # 9514e Full Text Show Details

o-Fluorbenzoylchlorid, 1) p-Chloranilin, ZnCl2, 2) H2SO4;

Hoffmann-La Roche

Patent: DE1145626 , 1963 ; Chem.Abstr., 1964 , vol. 60, # 12033h Full Text Show Details

/BRN= 636864/, /BRN= 471359/, ZnCl2;

Hoffmann-La Roche Inc.

Patent: US3203990 , 1962 ; Chem.Abstr., 1966 , vol. 64, # 3576f Full Text Show Details

Hoffmann-La Roche Inc.

Patent: US3109843 , 1962 ; Chem.Abstr., 1964 , vol. 60, # 2994a Full Text Show Details

Hoffmann - La Roche Inc.

Patent: US3121103 , 1961 ; Chem.Abstr., 1964 , vol. 61, # 5671f Full Text Show Details

Hoffmann - La Roche Inc.

Patent: US3121075 , 1961 ; Chem.Abstr., 1964 , vol. 61, # 5672d Full Text Show Details

p-Chlor-anilin, m-Fluorbenzoylchlorid;

Reeder; Sternbach

Patent: US3239564 , 1960 ; Chem.Abstr., 1966 , vol. 64, # 19498a Full Text Show Details

p-Chlor-anilin, 2-Fluorbenzoylchlorid;

Reeder; Sternbach

Patent: US3239564 , 1960 ; Chem.Abstr., 1966 , vol. 64, # 19498a Full Text Show Details

213

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Rx-ID: 8886866 Find similar reactions

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With zinc(II) chloride

T=200 - 230°C; 3 h;

Cortes Cortes; Salazar Franco; Garcia Mellado

Journal of Heterocyclic Chemistry, 2001 , vol. 38, # 3 p. 663 - 669 Title/Abstract Full Text View citing articles Show Details

Stage #1: With zinc(II) chloride

T=180 - 230°C; Friedel Crafts acylation; Stage #2: With sulfuric acid; acetic acid in water

0.666667 h; Reflux;

Cortez-Maya; Cortes Cortes; Hernandez-Ortega; Apan, T. Ramirez; Martinez-Garcia

Synthetic Communications, 2012 , vol. 42, # 1 p. 46 - 54 Title/Abstract Full Text View citing articles Show Details

214

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Rx-ID: 28175712 Find similar reactions

With hydrogenchloride in ethanol; water

Reflux;

Cheng, Pi; Zhang, Quan; Ma, Yun-Bao; Jiang, Zhi-Yong; Zhang, Xue-Mei; Zhang, Feng-Xue; Chen, Ji-Jun

Bioorganic and Medicinal Chemistry Letters, 2008 , vol. 18, # 13 p. 3787 - 3789 Title/Abstract Full Text View citing articles Show Details

Stage #1: With hydrogenchloride; water in ethanol

Reflux; Stage #2: With sodium hydrogencarbonate in ethanol; water

pH=8;

Cheng, Pi; Gu, Qiong; Liu, Wei; Zou, Jian-Feng; Ou, Yang-Yong; Luo, Zhong-Yong; Zeng, Jian-Guo

Molecules, 2011 , vol. 16, # 9 p. 7649 - 7661 Title/Abstract Full Text View citing articles Show Details

215

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Rx-ID: 31748601 Find similar reactions

Multi-step reaction with 2 steps 1.1: tert.-butyl lithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 1.25 h / -40 °C / Inert atmosphere 2.1: hydrogenchloride; water / ethanol / Reflux 2.2: pH 8 View Scheme

Cheng, Pi; Gu, Qiong; Liu, Wei; Zou, Jian-Feng; Ou, Yang-Yong; Luo, Zhong-Yong; Zeng, Jian-Guo

Molecules, 2011 , vol. 16, # 9 p. 7649 - 7661 Title/Abstract Full Text View citing articles Show Details

216

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Rx-ID: 31748639 Find similar reactions

Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / toluene / 20 °C 2.1: tert.-butyl lithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 2.2: 1.25 h / -40 °C / Inert atmosphere 3.1: hydrogenchloride; water / ethanol / Reflux 3.2: pH 8 View Scheme

Cheng, Pi; Gu, Qiong; Liu, Wei; Zou, Jian-Feng; Ou, Yang-Yong; Luo, Zhong-Yong; Zeng, Jian-Guo

Molecules, 2011 , vol. 16, # 9 p. 7649 - 7661 Title/Abstract Full Text View citing articles Show Details

217

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Rx-ID: 39047999 Find similar reactions

64%

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With 5,5'-dimethyl-2,2'-bipyridine; methanesulfonic acid; palladium (II) trifluoroacetate; water in 2methyl tetrahydrofuran

T=80°C; 36 h; Schlenk technique;

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Chen, Jiuxi; Ye, Leping; Su, Weike

Organic and Biomolecular Chemistry, 2014 , vol. 12, # 41 p. 8204 - 8211 Title/Abstract Full Text View citing articles Show Details

Synthesize

218

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Find similar Rx-ID: 28497541 Find similar reactions

B: 59%

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With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; copper(II) bis(trifluoromethanesulfonate); (R)-1,1'-binaphthyl-2,2'-diamine in toluene

T=80°C; 18 h; optical yield given as percent ee;

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Mannam, Sreedevi; Sekar, Govindasamy

Tetrahedron Asymmetry, 2009 , vol. 20, # 4 p. 497 - 502 Title/Abstract Full Text View citing articles Show Details

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219

Synthesize Find similar Rx-ID: 3092139 Find similar reactions

With potassium hydroxide

5 h; Heatinghydrolysis;

Schleuder; Patow; Richter

Pharmazie, 1983 , vol. 38, # 12 p. 882 - 883 Title/Abstract Full Text View citing articles Show Details

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220

Synthesize Find similar Rx-ID: 9458622 Find similar reactions

A: 26% D: 26%

Park, Kwanghee Koh; Lee, Jin Joo; Ryu, Jaegyung

Tetrahedron, 2003 , vol. 59, # 39 p. 7651 - 7659 Title/Abstract Full Text View citing articles Show Details

in acetonitrile

4 h; Irradiation;

221

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Find similar Rx-ID: 1182544 Find similar reactions

Find similar

(i) ZnCl2, (ii) aq. HCl, (iii) H2SO4; Multistep reaction;

Bogatskii,A.V. et al.

Pharmaceutical Chemistry Journal, 1977 , vol. 11, # 11 p. 1520 - 1525 Khimiko-Farmatsevticheskii Zhurnal, 1977 , vol. 11, # 11 p. 85 - 91 Full Text View citing articles Show Details

With sulfuric acid; acetic acid; zinc(II) chloride

2) H2O, reflux, 18 h; Yield given. Multistep reaction;

Vejdelek; Rajsner; Dlabac; et al.

Collection of Czechoslovak Chemical Communications, 1980 , vol. 45, # 12 p. 3593 - 3615 Title/Abstract Full Text View citing articles Show Details

With zinc(II) chloride

T=200 - 230°C; 3 h;

Cortes Cortes; Salazar Franco; Garcia Mellado

Journal of Heterocyclic Chemistry, 2001 , vol. 38, # 3 p. 663 - 669 Title/Abstract Full Text View citing articles Show Details

Hide Details

Stage #1: With zinc(II) chloride

T=205°C; Friedel-Crafts reaction; 2 h; Stage #2: With sulfuric acid

8 h; Heating;

Hu, Wenhui; Guo, Zongru; Chu, Fengming; Bai, Aiping; Yi, Xiang; Cheng, Guifang; Li, Jing

Bioorganic and Medicinal Chemistry, 2003 , vol. 11, # 7 p. 1153 - 1160 Title/Abstract Full Text View citing articles Show Details

Stage #1: With zinc(II) chloride

T=180 - 230°C; Friedel Crafts acylation; Stage #2: With sulfuric acid; acetic acid in water

0.666667 h; Reflux;

Cortez-Maya; Cortes Cortes; Hernandez-Ortega; Apan, T. Ramirez; Martinez-Garcia

Synthetic Communications, 2012 , vol. 42, # 1 p. 46 - 54 Title/Abstract Full Text View citing articles Show Details

With zinc(II) chloride

Singh, Rajesh K.; Prasad; Bhardwaj

Medicinal Chemistry Research, 2013 , vol. 22, # 12 p. 5901 - 5911 Title/Abstract Full Text View citing articles Show Details

222

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With toluene-4-sulfonic acid in xylene

223

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Rx-ID: 1375035 Find similar reactions

Hara,T. et al.

Journal of Organic Chemistry, 1978 , vol. 43, p. 4865 - 4869 Full Text View citing articles Show Details

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92%

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With iron; acetic acid in ethanol; water

T=60 - 70°C; 2 h;

Rx-ID: 1638692 Find similar reactions

Vejdelek; Rajsner; Dlabac; et al.

Collection of Czechoslovak Chemical Communications, 1980 , vol. 45, # 12 p. 3593 - 3615 Title/Abstract Full Text View citing articles Show Details

224

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Rx-ID: 3778685 Find similar reactions

With hydrogenchloride

0.5 h; Heatingacid hydrolysis;

Schutz; Fitz

Arzneimittel-Forschung/Drug Research, 1982 , vol. 32, # 3 p. 177 - 183 Title/Abstract Full Text View citing articles Show Details

With hydroxypropyl-α-cyclodextrin in water

0.75 h; Heating;

Kobetic, Renata; Jursic, Branko S; Bonnette, Sidney; Tsai, Jane S.-C; Salvatore, Salamone J

Tetrahedron Letters, 2001 , vol. 42, # 35 p. 6077 - 6082 Title/Abstract Full Text View citing articles Show Details

225

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44.2%

Rx-ID: 5972146 Find similar reactions

Guo, Zongru; Cheng, Guifang; Chu, Fengming

Patent: US2004/58977 A1, 2004 ; Location in patent: Page/Page column 15 ; Title/Abstract Full Text Show Details

o-ClC6H4COCl, p-ClC6H4NH2, ZnCl2;

Hoffmann-La Roche

Patent: US3123529 , 1962 ; Chem.Abstr., 1964 , vol. 60, # 12035 Full Text Show Details

Entspr. Anilin, o-Chlorbenzoylchlorid;

Reeder; Sternbach

Patent: US3239564 , 1960 ; Chem.Abstr., 1966 , vol. 64, # 19498a Full Text Show Details

Hide Details

Methyl-N-<4-chlor-2-o-chlorbenzoyl>phenylcarbamat, meth.KOH, Δ (a);

John Wyeth and Broth.

Patent: DE2553622 , 1976 ; Chem.Abstr., vol. 85, # 77930 Full Text Show Details

3-o-Chlorphenyl-5-chloroxindol, 1.)NaHCO3, 2.)O2(g), 3.)H2O/Δ (b);

John Wyeth and Broth.

Patent: DE2553622 , 1976 ; Chem.Abstr., vol. 85, # 77930 Full Text Show Details

2-Chlor-benzoylchlorid u. 4-Chlor-anilin + ZnCl2 (220-230grad, 1-2h);

Sternbach et al.

Journal of Organic Chemistry, 1961 , vol. 26, p. 4488,4494 Full Text Show Details

(yield)80percent;

Sternbach et al.

Journal of Organic Chemistry, 1961 , vol. 26, p. 4488,4494 Full Text Show Details

2-Chlor-benzoylchlorid, 1) 4-Chlor-anilin, ZnCl2, 2) sd. Eg., H2SO4;

Hoffmann-La Roche

Patent: DE1136709 , 1962 ; Chem.Abstr., 1963 , vol. 59, # 12827 Full Text Show Details

2-Chlor-benzoylchlorid, 4-Chlor-anilin, ZnCl2;

Reeder; Sternbach

Patent: US3141890 , 1962 ; Chem.Abstr., 1964 , vol. 61, # 9514e Full Text Show Details

Reeder; Sternbach

Patent: US3136815 , 1960 ; Chem.Abstr., 1964 , vol. 61, # 9515f Full Text Show Details

Lorazepam, Saeure;

Schillings et al.

Arzneimittel Forschung, 1971 , vol. 21, p. 1059,1061,1062 Full Text Show Details

entspr. RCOCl, entspr. RNH2;

Hoffmann-La Roche

Patent: CH408029 , 1966 ; Chem.Abstr., vol. 66, # 55532 Full Text Show Details

o-Chlorbenzoylchlorid, p-Chloranilin, ZnCl2;

F.Hoffmann La Roche and Co AG

Patent: CH414652US3427304 , 1966 ; Full Text Show Details

226

Hoffmann-La Roche Inc.

Patent: US3109843 , 1962 ; Chem.Abstr., 1964 , vol. 60, # 2994a Full Text Show Details

Synthesize Find similar

Multi-step reaction with 2 steps 1.1: SOCl2 / Heating 2.1: ZnCl2 / 2 h / 205 °C 2.2: 7- percent H2SO4 / 8 h / Heating View Scheme

Rx-ID: 14315633 Find similar reactions

Hu, Wenhui; Guo, Zongru; Chu, Fengming; Bai, Aiping; Yi, Xiang; Cheng, Guifang; Li, Jing

Bioorganic and Medicinal Chemistry, 2003 , vol. 11, # 7 p. 1153 - 1160 Title/Abstract Full Text View citing articles Show Details

227

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Multi-step reaction with 2 steps 1: 12 percent / KOH, K2CO3, H2O / benzene; methanol / 2 h / Ambient temperature 2: 92 percent / Fe/AcOH / H2O; ethanol / 2 h / 60 - 70 °C View Scheme

Rx-ID: 21324265 Find similar reactions

Vejdelek; Rajsner; Dlabac; et al.

Collection of Czechoslovak Chemical Communications, 1980 , vol. 45, # 12 p. 3593 - 3615 Title/Abstract Full Text View citing articles Show Details

228

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Multi-step reaction with 2 steps 1: 12 percent / KOH, K2CO3, H2O / benzene; methanol / 2 h / Ambient temperature 2: 92 percent / Fe/AcOH / H2O; ethanol / 2 h / 60 - 70 °C View Scheme

Rx-ID: 21351079 Find similar reactions

Vejdelek; Rajsner; Dlabac; et al.

Collection of Czechoslovak Chemical Communications, 1980 , vol. 45, # 12 p. 3593 - 3615 Title/Abstract Full Text View citing articles Show Details

229

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Rx-ID: 28175713 Find similar reactions

With hydrogenchloride in ethanol; water

Reflux;

Cheng, Pi; Zhang, Quan; Ma, Yun-Bao; Jiang, Zhi-Yong; Zhang, Xue-Mei; Zhang, Feng-Xue; Chen, Ji-Jun

Bioorganic and Medicinal Chemistry Letters, 2008 , vol. 18, # 13 p. 3787 - 3789 Title/Abstract Full Text View citing articles Show Details

Stage #1: With hydrogenchloride; water in ethanol

Reflux; Stage #2: With sodium hydrogencarbonate in ethanol; water

pH=8;

Cheng, Pi; Gu, Qiong; Liu, Wei; Zou, Jian-Feng; Ou, Yang-Yong; Luo, Zhong-Yong; Zeng, Jian-Guo

Molecules, 2011 , vol. 16, # 9 p. 7649 - 7661 Title/Abstract Full Text View citing articles Show Details

230

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Rx-ID: 31748602 Find similar reactions

Cheng, Pi; Gu, Qiong; Liu, Wei; Zou, Jian-Feng; Ou, Yang-Yong; Luo, Zhong-Yong; Zeng, Jian-Guo

Molecules, 2011 , vol. 16, # 9 p. 7649 - 7661 Title/Abstract Full Text View citing articles Show Details

231

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232

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Rx-ID: 31748640 Find similar reactions

Cheng, Pi; Gu, Qiong; Liu, Wei; Zou, Jian-Feng; Ou, Yang-Yong; Luo, Zhong-Yong; Zeng, Jian-Guo

Molecules, 2011 , vol. 16, # 9 p. 7649 - 7661 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 39048000 Find similar reactions

52%

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With 5,5'-dimethyl-2,2'-bipyridine; methanesulfonic acid; palladium (II) trifluoroacetate; water in 2methyl tetrahydrofuran

T=80°C; 36 h; Schlenk technique;

Chen, Jiuxi; Ye, Leping; Su, Weike

Organic and Biomolecular Chemistry, 2014 , vol. 12, # 41 p. 8204 - 8211 Title/Abstract Full Text View citing articles Show Details

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233

Synthesize Find similar Rx-ID: 32435181 Find similar reactions

A: 0.14 g B: 0.035 g

Leardini, Rino; McNab, Hamish; Nanni, Daniele; Tenan, Anton G.; Thomson, Andrew

Organic and Biomolecular Chemistry, 2012 , vol. 10, # 3 p. 623 - 630 Title/Abstract Full Text View citing articles Show Details

T=155 - 650°C; P=0.023 Torr; 0.416667 h; Pyrolysis;

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234

With aluminium trichloride; benzene

Rx-ID: 7919858 Find similar reactions

Hayashi et al.

Bulletin of the Chemical Society of Japan, 1936 , vol. 11, p. 186 Chem. Zentralbl., 1936 , vol. 107, # II p. 1720 Full Text Show Details

235

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Rx-ID: 615590 Find similar reactions

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With zinc(II) chloride

T=100 - 180°C; dann auf 200-230grad und Kochen des Reaktionsproduktes mit Alkohol und konz. Salzsaeure;

Angel

Journal of the Chemical Society, 1912 , vol. 101, p. 516 Full Text Show Details

Stage #1: With zinc(II) chloride

T=205°C; Friedel-Crafts reaction; 2 h; Stage #2: With sulfuric acid

8 h; Heating;

Hu, Wenhui; Guo, Zongru; Chu, Fengming; Bai, Aiping; Yi, Xiang; Cheng, Guifang; Li, Jing

Bioorganic and Medicinal Chemistry, 2003 , vol. 11, # 7 p. 1153 - 1160 Title/Abstract Full Text View citing articles Show Details

200 mg

Stage #1: With zinc(II) chloride

T=180 - 205°C; 2 h; Stage #2: With hydrogenchloride in water

T=120°C; Reflux; Hide Experimental Procedure

Commissariat A L'Energie Atomique Et Aux Energies Alternatives; Lopez, Roman; Hebbe, Severine; Gillet, Daniel; Barbier, Julien

Patent: US2016/83355 A1, 2016 ; Location in patent: Paragraph 0339 ; Title/Abstract Full Text Show Details

1:2-benzoyl-4-bromoaniline

2-benzoyl-4-bromoaniline Pathway 1: 4-bromoaniline (1 eq., 0.05 mol, 8.6 g) is dissolved in benzoyl chloride (2.7 eq., 0.135 mol, 15.7 ml). The reaction mixture is heated to 180° C. and then zinc chloride (1.25 eq., 0.063 mol, 8.5 g) is added. After heating for two hours at 205° C., the mixture is cooled to 120° C. and then 60 ml of 3N hydrochloric acid are added. After refluxing and separation of the hot acid layer by settling out, the water-insoluble residue is dissolved in 80 ml of 70percent sulfuric acid, brought to reflux for 8 hours, and then poured into a large amount of ice-cold water. After the addition of ethyl acetate (3×50 ml), the organic phases are combined and then evaporated. After purification by HPLC, the yield is less than 1percent (the mass obtained was approximately 200 mg).

236

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90%

With hydrogenchloride in ethanol

T=80°C;

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Rx-ID: 2667361 Find similar reactions

Mazurov, A. A.; Antonenko, V. V.; Andronati, S. A.

Chemistry of Heterocyclic Compounds (New York, NY, United States), 1983 , vol. 19, # 3 p. 337 - 340 Khimiya Geterotsiklicheskikh Soedinenii, 1983 , # 3 p. 411 - 414 Title/Abstract Full Text View citing articles Show Details

237

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Rx-ID: 3599440 Find similar reactions

97%

With trimethylsilyl iodide; water in acetonitrile

T=20°C; 0.25 h;

Boruah, Monalisa; Konwar, Dilip

Journal of Chemical Research - Part S, 2002 , # 12 p. 601 - 603 Title/Abstract Full Text View citing articles Show Details

94%

With water; iron

T=80 - 100°C; 5 h; Hide Experimental Procedure

CHATTOPADHYAYA, Jyoti; UPADHAYAYA, Ram Shankar

Patent: WO2009/91324 A1, 2009 ; Location in patent: Page/Page column 48 ; Title/Abstract Full Text Show Details

Preparation of 2-Amino-5-bromo benzophenone; To a hot (80-100 0C) solution of the 5-bromo-3-phenyl-benzo[c]isooxazole (20.0 g, 73.0 mmol) m glacial acetic acid (550 InL)1 iron powder (45.0 g, 802.0 mmol) and water (275 mL) were added m portions for a period of 2 h. After heating for 3 h, the brown solution was poured into a mixture of water and crushed ice, stirred well, the golden yellow precipitate was filtered under suction, washed with water until the washings became colorless and dried under reduced pressure to obtain 2-ammo-5-bromo- benzophenone (19.50 g, 94percent) as a golden yellow solid, Mp 112-113 0C. 1H NMR (400 MHz, CDCl3): δ 5.90-6 25 (br s, 2 H, D2O exchangeable), 6.72 (d, J = 8.80 Hz, 1 H), 7.37 (dd, J= 1 1.7, 2.3 Hz, 1 H),

7.47 (t, J= 7 8 Hz, 2 H), 7.51 -7.58 (m, 2 H), 7 59-7.64 (m, 2 H)

92%

With aluminium trichloride; zinc in tetrahydrofuran

6 h; Ambient temperature;

Dutta, Dilip Kumar; Konwar, Dilip

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1994 , vol. 33, # 7 p. 690 - 691 Title/Abstract Full Text Show Details

Hide Details

89%

With Saccharomyces cerevisiae bakers' yeast in methanol

T=20°C; pH=7; 6 h; aq. phosphate bufferMicrobiological reactionshaking;

Lekhok, Kushal C.; Prajapati, Dipak; Boruah, Ramesh C.; Mazumder, Sharbani; Borah, Tarun C.

Monatshefte fur Chemie, 2009 , vol. 140, # 10 p. 1183 - 1187 Title/Abstract Full Text View citing articles Show Details

86%

With samarium; iodine in tetrahydrofuran

T=20°C; 0.0833333 h;

Fan, Xuesen; Zhang, Yongmin

Tetrahedron Letters, 2002 , vol. 43, # 39 p. 7001 - 7003 Title/Abstract Full Text View citing articles Show Details

86%

With samarium diiodide in tetrahydrofuran

T=20°C; 0.0833333 h;

Fan, Xuesen; Zhang, Xinying; Zhang, Yongmin

Heteroatom Chemistry, 2005 , vol. 16, # 7 p. 637 - 643 Title/Abstract Full Text View citing articles Show Details

70%

With iron; acetic acid in water

2.5 h; Heating;

Mamo, Antonino; Nicoletti, Salvatore; Tat, N. Cam

Molecules, 2002 , vol. 7, # 8 p. 618 - 627 Title/Abstract Full Text View citing articles Show Details

With trimethylsilyl iodide; water

1.) chloroform, room temperature, 2 h, 2.) 1 h; Yield given. Multistep reaction;

Konwar, D.; Boruah, R. C.; Sandhu, J. S.; Baruah, J. N.

Synthetic Communications, 1984 , vol. 14, # 11 p. 1053 - 1058 Title/Abstract Full Text Show Details

238

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19.8%

Rx-ID: 5824130 Find similar reactions

Guo, Zongru; Cheng, Guifang; Chu, Fengming

Patent: US2004/58977 A1, 2004 ; Location in patent: Page/Page column 15 ; Title/Abstract Full Text Show Details

14%

Hide Experimental Procedure

Ungashe, Solomon; Wei, Zheng; Wright, J. J.; Pennell, Andrew; Premack, Brett; Schall, Thomas

Patent: US2005/137179 A1, 2005 ; Title/Abstract Full Text Show Details

5:Synthesis of (2-Amino-5-bromo-phenyl)-phenyl-methanone

Example 5 Synthesis of (2-Amino-5-bromo-phenyl)-phenyl-methanone To BCl3 (1 M in DCM) (48 mL, 48 mmol), cooled to 0° C., was added dropwise a solution of 4-bromoaniline (5.5 g, 32 mmol) in 60 mL of TCE over a period of 15 min and stirred at that temperature for an additional 10 min. Benzonitrile (4.12 g, 40 mmol) and AlCl3 (6.0 g, 45 mmol) were added under ice-water cooling. The solution was allowed to warm to RT and stirred for 30 min. The solution was then heated at 80-90° C. for 1 h and the DCM distilled off. The resulting solution was refluxed at 160° C. for 4 h and stirred at rt overnight. 3N HCl (40 ml approx.) was added and the reaction mixture stirred at 90° C. for 1 hr. The reaction mixture was allowed to cool to RT and the solution was brought to pH12 by addition of 6N aq. NaOH soln. The reaction mixture was diluted with water and DCM. The resulting two layers were separated and the aqueous layer was extracted with DCM (2*150 mL) and dried over Na2SO4. After removal of solvent, the residue was purified by the flash chromatography using ethyl acetate/hexane (1:12) as eluent. 1.2 g of the pure product was obtained as yellow solid (yield=14percent).

Taylor; Heindel

Journal of Organic Chemistry, 1967 , vol. 32, p. 1666 Full Text View citing articles Show Details

Golovenko Ya.; Bogatskii; Kolomeichenko Yu.; et al.

Doklady Biochemistry, 1978 , vol. 238, # 1-6 p. 34 - 36 Title/Abstract Full Text View citing articles Show Details

Staskun

Journal of Organic Chemistry, 1964 , vol. 29, p. 2856 Full Text View citing articles Show Details

Technochemie

Patent: DE2400689 , 1974 ; Chem.Abstr., 1976 , vol. 84, # 43633 Full Text Show Details

Hide Details

With n-butyllithium in tetrahydrofuran; cyclohexanes

T=-100 - -70°C; Nitrogen atmosphere; Hide Experimental Procedure

MILLENNIUM PHARMACEUTICALS, INC.

Patent: WO2003/99773 A1, 2003 ; Location in patent: Page 56-57 ; Title/Abstract Full Text Show Details

4:Procedure B (General synthesis of substituted [2-AMINOBENZOPHENONES)] :; Example 4: (2-Amino-5-bromo-phenyl) -phenyl-methanone

A substituted Weinreb amide (10 mmol) and a substituted bromobenzene (10 mmol) were dissolved in THF under nitrogen. The reaction mixture was cooled to-100 [°C] using a liquid nitrogen/diethyl ether bath. n-BuLi (21 mmol, 1.6 M in cyclohexanes) was introduced via syringe over a period of twenty minutes. The reaction mixture was allowed to warm to-70 [°C] and then quenched by adding of 21 [ML] of 1 N [HC1.] The reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer was washed with saturated sodium chloride, then concentrated to a residue. The residue was chromatographed on silica gel using 1: 1 ethyl acetate: hexanes to give the product. Typical yields are 30-60percent.

239

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74%

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Rx-ID: 9498044 Find similar reactions

With sodium hydroxide in 1,4-dioxane

5 h; Heating;

Kulikov; Pavlovsky; Mazepa; Andronati

Chemistry of Heterocyclic Compounds, 2003 , vol. 39, # 4 p. 485 - 492 Title/Abstract Full Text View citing articles Show Details

240

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Rx-ID: 10440373 Find similar reactions

96%

With sodium perborate; ammonium molybdate(VI) tetrahydrate; potassium bromide in acetic acid

T=0°C; 3 h;

Atechian, Sarkis; Nock, Nadine; Norcross, Roger D.; Ratni, Hassen; Thomas, Andrew W.; Verron, Julien; Masciadri, Raffaello

Tetrahedron, 2007 , vol. 63, # 13 p. 2811 - 2823 Title/Abstract Full Text View citing articles Show Details

96%

With sodium perborate; ammonium molibdate; potassium bromide in acetic acid

T=0°C; 3 h; Hide Experimental Procedure

Malherbe, Parichehr; Masciadri, Raffaello; Norcross, Roger David; Ratni, Hasane; Thomas, Andrew William

Patent: US2006/94754 A1, 2006 ; Location in patent: Page/Page column 11 ; Title/Abstract Full Text Show Details

A.16:(2-Amino-5-bromo-phenyl)-phenyl-methanone

Example A16 (2-Amino-5-bromo-phenyl)-phenyl-methanone The title compound is known from US 20040127536 A1 and was prepared according to a method developed by D. Roche, K. Prasad, O. Repic, T. J. Blacklock, Tetrahedron Lett. 41, 2083-2085 (2000). 2-Aminobenzophenone (30 g, 152 mmol) was suspended in acetic acid (300 mL). Potassium bromide (19.9 g, 167 mmol), sodium perborate tetrahydrate (28 g, 183 mmol) and ammonium molybdate tetrahydrate (1.5 g) were added and stirring continued for 3 hours at 0° C. The dense yellow precipitate which formed was diluted with ice water (300 mL) and then filtered off and washed with ice water and dried. One obtained 40.3 g (96percent) of a yellow solid. MS: m/z=276 (M).

88%

With NaBO3*4H2O; acetic acid; potassium bromide

T=0°C; 3 h;

Zhang, Jintang; Zhu, Dapeng; Yu, Chenmin; Wan, Changfeng; Wang, Zhiyong

Organic Letters, 2010 , vol. 12, # 12 p. 2841 - 2843 Title/Abstract Full Text View citing articles Show Details

Hide Details

88%

With sodium 1,2,3-dioxaboriran-3-olate tetrahydrate; ammonium molybdophosphate tetrahydrate; acetic acid; potassium bromide

T=0°C; 3 h;

Zhang, Jintang; Yu, Chenmin; Wang, Sujing; Wan, Changfeng; Wang, Zhiyong

Chemical Communications, 2010 , vol. 46, # 29 p. 5244 - 5246 Title/Abstract Full Text View citing articles Show Details

85.71%

With N-Bromosuccinimide in dichloromethane; water

T=-10°C; 2.16667 h;

China Pharmaceutical University; Zhang, Huibin; Zhou, Jinpei; Zhao, Leilei; Xu, Bin; Han, Li; Yang, Yifei

Patent: CN105541825 A, 2016 ;

Hide Experimental Procedure

Location in patent: Paragraph 0064; 0065; 0066; 0067; 0068; 0069 ; Title/Abstract Full Text Show Details

1.a:

2-amino-benzophenone (5g, 25.35mmol) was dissolved in 60ml of dichloromethane, stirred for 10min at -10 cold trap, was added portionwise N- bromosuccinimide (4.74g, after 26.62mmol), reaction was continued for 2 hours in the cold trap, was added 30ml of water, extracted with dichloromethane, washed with brine, and the organic layer was collected, dried over anhydrous sodium sulfate, the organic solvent was distilled off under reduced pressure, the residue was purified by a silica gel column purified by chromatography, using petroleum ether / ethyl acetate (V / V = 20 / 1-10 / 1)to afford 2-amino-5-bromo-benzophenone 6g, as a yellow solid, a yield of 85.71percent 83%

With N-Bromosuccinimide; sulfonic acid functionalized silica in diethyl ether; acetonitrile

T=20°C; 0.5 h;

Das, Biswanath; Venkateswarlu, Katta; Krishnaiah, Maddeboina; Holla, Harish

Tetrahedron Letters, 2006 , vol. 47, # 49 p. 8693 - 8697 Title/Abstract Full Text View citing articles Show Details

82%

With N-Bromosuccinimide in diethyl ether; acetonitrile

T=25°C; 0.5 h; regiospecific reaction;

Patterson, Stephen; Alphey, Magnus S.; Jones, Deuan C.; Shanks, Emma J.; Street, Ian P.; Frearson, Julie A.; Wyatt, Paul G.; Gilbert, Ian H.; Fairlamb, Alan H.

Journal of Medicinal Chemistry, 2011 , vol. 54, # 19 p. 6514 - 6530 Title/Abstract Full Text View citing articles Show Details

80%

With N-Bromosuccinimide

T=20°C; 0.416667 h; regioselective reaction;

Venkateswarlu, Katta; Suneel, Kanaparthy; Das, Biswanath; Reddy, Kuravallapalli Nagabhushana; Reddy, Thummala Sreenivasulu

Synthetic Communications, 2009 , vol. 39, # 2 p. 215 - 219 Title/Abstract Full Text View citing articles Show Details

With tetra-N-butylammonium tribromide in chloroform

T=20°C;

Siemssen, Brent; Kim, Ki-Won; Kim, Min-Sook; Kim, Byung-Soo; Cho, Seong-Jin; Park, Dong-Kyu; Woo, Hyung-Suk; Kwon, Tae-Woo

Molecular Crystals and Liquid Crystals, 2007 , vol. 462, # 1 p. 159 - 167 Title/Abstract Full Text View citing articles Show Details

With N-Bromosuccinimide in dichloromethane

T=-10°C; Hide Experimental Procedure

JANSSEN PHARMACEUTICA, N.V.

Patent: WO2005/9967 A2, 2005 ; Location in patent: Page/Page column 58 ; Title/Abstract Full Text Show Details

57.a:

a) (2-Amino-5-bromo-phenyl)-phenyl-methanone A flask charged with (2-amino-phenyl) -phenyl-methanone (5 g, 25 mmol) and DCM (80 mL) was cooled to-10 °C and NBS (4.5 g, 25 mmol) was added over 30 minutes via an addition funnel. The reaction was complete following addition of NBS and the reaction was diluted with 80 mL of DCM, washed with sat NAHC03 (2 x 100 mL), dried over NA2SO4 and concentrated to give 7 g of a crude product which was used without further purification.

With N-Bromosuccinimide in dichloromethane

T=-10°C; 2.5 h; Hide Experimental Procedure

BOEHRINGER INGELHEIM INTERNATIONAL GMBH; SMETHURST, Christian; ENGELHARDT, Harald; GIANNI, Davide; REISER, Ulrich

Patent: WO2014/154762 A1, 2014 ; Location in patent: Page/Page column 36-37 ; Title/Abstract Full Text Show Details

(2-Amino-5-bromo-phenyl)-phenyl-methanone To a solution of (2-Amino-phenyl)-phenyl-methanone (5 g, 25 mmol) in DCM (100 mL) is cooled to -10 °C, then NBS (4.512 g, 25 mmol) is added in 30 minites. After the addition the mixture is stirred at -10 °C for 2 h. The mixture is diluted with DCM, washed with salt NaHC03 (2 x 100 mL), salt NaCl (100 mL), dried over anhydrous Na2S04, filtered and concentrated to give product (6.3 g), which is used for the next step without further purification. TLC (10: 1, petrol ether/ethyl acetate) Rf = 0.6 6.3 g

With N-Bromosuccinimide in dichloromethane

T=-10°C; 2.5 h; Hide Experimental Procedure

BOEHRINGER INGELHEIM INTERNATIONAL GMBH; SMETHURST, Christian; ENGELHARDT, Harald; GIANNI, Davide; REISER, Ulrich

Patent: US2014/296230 A1, 2014 ; Location in patent: Paragraph 0141-0143 ; Title/Abstract Full Text Show Details

1:(2-Amino-5-bromo-phenyl)-phenyl-methanone

To a solution of (2-Amino-phenyl)-phenyl-methanone (5 g, 25 mmol) in DCM (100 mL) is cooled to -10° C., then NBS (4.512 g, 25 mmol) is added in 30 minutes. After the addition the mixture is stirred at -10° C. for 2 h. The mixture is diluted with DCM, washed with salt NaHCO3 (2*100 mL), salt NaCl (100 mL), dried over anhydrous Na2SO4, filtered and concentrated to give product (6.3 g), which is used for the next step without further purification. TLC (10:1, petrol ether/ethyl acetate) Rf=0.6 80 mg

With sodium perborate; ammonium molybdate; acetic acid; potassium bromide

T=0°C; 16 h; Hide Experimental Procedure

CONVERGENE LLC; VANKAYALAPATI, Hariprasad; YOSHIOKA, Makoto; STROVEL, Jeffrey William; PADIA, Janak Khimchand

Patent: WO2014/159837 A1, 2014 ; Location in patent: Page/Page column 76 ; Title/Abstract Full Text Show Details

17:

2-aminophenyl)(phenyl)methanone (500 mg) was reacted with KBr, ammonium molbedate, and sodium per borate in AcOH at 0°C for 16 hours to yield (2-amino-5- bromophenyl)(phenyl)methanone (80 mg).

With N-Bromosuccinimide in dichloromethane

T=0 - 20°C; 3 h; Inert atmosphere; regioselective reaction;

Abdelkafi, Hajer; Michau, Aurélien; Clerget, Alexandra; Buisson, David-Alexandre; Johannes, Ludger; Gillet, Daniel; Barbier, Julien; Cintrat, Jean-Christophe

ChemMedChem, 2015 , vol. 10, # 7 p. 1153 - 1156 Title/Abstract Full Text View citing articles Show Details

241

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Multi-step reaction with 2 steps 1.1: potassium hydroxide / methanol / 20 °C 1.2: 66 percent / methanol; tetrahydrofuran / Heating 2.1: 70 percent / acetic acid; iron / H2O / 2.5 h / Heating View Scheme

Rx-ID: 14259198 Find similar reactions

Mamo, Antonino; Nicoletti, Salvatore; Tat, N. Cam

Molecules, 2002 , vol. 7, # 8 p. 618 - 627 Title/Abstract Full Text View citing articles Show Details

242

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Rx-ID: 14264696 Find similar reactions

Mamo, Antonino; Nicoletti, Salvatore; Tat, N. Cam

Molecules, 2002 , vol. 7, # 8 p. 618 - 627 Title/Abstract Full Text View citing articles Show Details

243

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Rx-ID: 22840608 Find similar reactions

31%

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With hydrogenchloride in tetrahydrofuran; diethyl ether; water

T=0 - 50°C; 18 h;

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American Home Products Corporation; Ligand Pharmaceuticals, Inc.

Patent: US6358948 B1, 2002 ; Location in patent: Example 17 ;

Title/Abstract Full Text Show Details

244

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Rx-ID: 24198687 Find similar reactions

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Wyeth; Ligand Pharmaceuticals, Inc.

Patent: US6498154 B1, 2002 ;

in tetrahydrofuran; ethyl acetate

Hide Experimental Procedure

Title/Abstract Full Text Show Details

17:3-[(2R,4S)-2,4-Dimethyl-4-phenyl-1,4-dihydro-2H-3,1-benzoxazin-6-yl]-5-fluorobenzonitrile

EXAMPLE 17 3-[(2R,4S)-2,4-Dimethyl-4-phenyl-1,4-dihydro-2H-3,1-benzoxazin-6-yl]-5-fluorobenzonitrile To a solution of 2-amino-4-bromobenzonitrile (5 g, 25 mmol) in anhydrous THF, was added at 0° C. under nitrogen, phenylmagnesium bromide (3 M in ether, 25 mL, 75 mmol). The mixture was allowed to warm to room temperature, stirred under nitrogen for 15 hours, and treated with 2N aqueous hydrogen chloride solution (100 mL). The aqueous solution was heated to 50° C. for 3 hours, cooled to room temperature, and neutralized with a cold saturated sodium bicarbonate solution. Ethyl acetate (100 mL) was added and the organic layer was separated and aqueous layer was extracted with ethyl acetate (3*40 mL). The combined organic layers were dried (MgSO4) and evaporated. The residue was purified by a flash column chromatography(silica gel, hexane:ethyl acetate/4:1) to yield (2-amino-5-bromophenyl)(phenyl)methanone as a yellow crystal (2.13 g, 31percent): MS (ESI) m/z 276/278 (M+H)+.

245

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Rx-ID: 28941514 Find similar reactions

246

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Stage #1: bromobenzene With n-butyllithium in tetrahydrofuran; hexane

T=-78°C; Inert atmosphere; Stage #2: 2-amino-5-bromo-N-methoxy-N-methyl-benzamide in tetrahydrofuran; hexane

T=-78°C; Inert atmosphere;

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Kraus, James M.; Verlinde, Christophe L. M. J.; Karimi, Mandana; Lepesheva, Galina I.; Gelb, Michael H.; Buckner, Frederick S.

Journal of Medicinal Chemistry, 2009 , vol. 52, # 6 p. 1639 - 1647 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 31415136 Find similar reactions

60%

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Stage #1: in tetrahydrofuran; diethyl ether

T=0°C; Stage #2: With ammonium chloride in tetrahydrofuran; diethyl ether; water

Hide Experimental Procedure

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Maezaki, Hironobu; Banno, Yoshihiro; Miyamoto, Yasufumi; Moritou, Yuusuke; Asakawa, Tomoko; Kataoka, Osamu; Takeuchi, Koji; Suzuki, Nobuhiro; Ikedo, Koji; Kosaka, Takuo; Sasaki, Masako; Tsubotani, Shigetoshi; Tani, Akiyoshi; Funami, Miyuki; Yamamoto, Yoshio; Tawada, Michiko; Aertgeerts, Kathleen; Yano, Jason; Oi, Satoru

Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 15 p. 4482 - 4498 Title/Abstract Full Text View citing articles Show Details

5.1.3. (2-Amino-5-bromophenyl)(phenyl)methanone (5a)

To a solution of 5.0 g (19 mmol) of 2-amino-5-bromo-N-methoxy-N-methylbenzamide (4a) in 50 mL of diethyl ether was added 24 mL (48 mmol) of 2 M phenylmagnesium bromide in THF dropwise at 0 °C. The resulting mixture was stirred at 0 °C for 15 min. After quenching with saturated aqueous ammonium chloride solution, the reaction mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. Purification by column chromatography (silica gel, eluting at a gradient of 5-25percent ethyl acetate in hexanes) afforded 3.21 g (60percent) of the title compound as yellow crystals. 1H NMR (200 MHz, CDCl3) δ: 6.08 (br s, 2H), 6.65 (d, J = 8.8 Hz, 1H), 7.26-7.66 (m, 7H).

247

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Multi-step reaction with 2 steps 1.1: triethylamine / ethanol / 0.5 h / 20 °C 1.2: 17 h / 75 °C 2.1: tetrahydrofuran; diethyl ether / 0 °C View Scheme

Rx-ID: 31415524 Find similar reactions

Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 15 p. 4482 - 4498 Title/Abstract Full Text View citing articles Show Details

248

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Multi-step reaction with 3 steps 1.1: tetrahydrofuran / 4 h / Reflux 2.1: triethylamine / ethanol / 0.5 h / 20 °C

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Rx-ID: 31415759 Find similar reactions

Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 15 p. 4482 - 4498

2.2: 17 h / 75 °C 3.1: tetrahydrofuran; diethyl ether / 0 °C View Scheme

Title/Abstract Full Text View citing articles Show Details

249

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Multi-step reaction with 3 steps 1: hydrogenchloride; iron / ethanol; water / 2 h / 80 °C 2: tetrahydrofuran; diethyl ether 3: CuCl2*H2O; potassium carbonate / N,N-dimethyl-formamide / 24 h / 60 °C View Scheme

Rx-ID: 31460311 Find similar reactions

Yan, Yizhe; Wang, Zhiyong

Chemical Communications, 2011 , vol. 47, # 33 p. 9513 - 9515 Title/Abstract Full Text View citing articles Show Details

250

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Multi-step reaction with 2 steps 1: tetrahydrofuran; diethyl ether 2: CuCl2*H2O; potassium carbonate / N,N-dimethyl-formamide / 24 h / 60 °C View Scheme

Rx-ID: 31460317 Find similar reactions

Yan, Yizhe; Wang, Zhiyong

Chemical Communications, 2011 , vol. 47, # 33 p. 9513 - 9515 Title/Abstract Full Text View citing articles Show Details

251

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With CuCl2*H2O; potassium carbonate in N,N-dimethyl-formamide

T=60°C; 24 h;

Rx-ID: 31460331 Find similar reactions

Yan, Yizhe; Wang, Zhiyong

Chemical Communications, 2011 , vol. 47, # 33 p. 9513 - 9515 Title/Abstract Full Text View citing articles Show Details

252

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Rx-ID: 38015790 Find similar reactions

90%

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With para-nitrobenzenesulfonic acid; palladium diacetate in tetrahydrofuran; water

T=80°C; 48 h; Inert atmosphereSchlenk technique; Hide Experimental Procedure

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Chen, Jiuxi; Li, Jianjun; Su, Weike

Molecules, 2014 , vol. 19, # 5 p. 6439 - 6449 Title/Abstract Full Text View citing articles Show Details

General Procedure for the Synthesis of o-Aminobenzophenones

General procedure: Under a N2 atmosphere, a Schlenk tube was charged with 2-aminobenzonitrile 1 (0.3 mmol),sodium arylsulfinate 2 (0.6 mmol), Pd(OAc)2 (10 mol percent), bpy (20 mol percent), p-NBSA (10 equiv), THF (2 mL), and H2O (1 mL) at room temperature. The reaction mixture was stirred vigorously at 80 °C for 48 h. The mixture was poured into ethyl acetate, which was washed with saturated NaHCO3 (2 × 10 mL) and then brine (1 × 10 mL). After the aqueous layer was extracted with ethyl acetate, the combined organic layers were dried over anhydrous MgSO4 and evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane/ethyl acetate) to afford the desired products 3.

253

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Rx-ID: 39047994 Find similar reactions

94%

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With 5,5'-dimethyl-2,2'-bipyridine; methanesulfonic acid; palladium (II) trifluoroacetate; water in 2methyl tetrahydrofuran

T=80°C; 36 h; Schlenk technique;

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Chen, Jiuxi; Ye, Leping; Su, Weike

Organic and Biomolecular Chemistry, 2014 , vol. 12, # 41 p. 8204 - 8211 Title/Abstract Full Text View citing articles Show Details

254

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Rx-ID: 42540372 Find similar reactions

100%

in dichloromethane

T=0 - 20°C;

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Commissariat A L'Energie Atomique Et Aux Energies Alternatives; Lopez, Roman; Hebbe, Severine; Gillet, Daniel; Barbier, Julien

Patent: US2016/83355 A1, 2016 ;

Location in patent: Paragraph 0340; 0341; 0342; 0343 ;

Hide Experimental Procedure

Title/Abstract Full Text Show Details

1:2-benzoyl-4-bromoaniline

2-benzoyl-4-bromoaniline Pathway 2: 2-aminobenzophenone (1 eq., 5 mmol, 0.986 g) is dissolved in dichloromethane at 0° C. N-bromosuccinimide (1 eq., 5 mmol, 0.890 g) is then added in small portions. The temperature of the reaction mixture is allowed to return to ambient temperature over approximately two hours. The reaction mixture is then evaporated and 2-benzoyl-4-bromoaniline is quantitatively obtained. 1H NMR (400 MHz, CDCl ) δ: 7.64-7.63 (d, J=7.2 Hz, 2H, 2′), 7.56 (s, 1H, 6), 7.55-7.54 (d, J=2.4 Hz, 1H, 4′), 7.50-7.47 (t, J=7.6 Hz, 2H, 3′), 7.38-7.35 (q, J=8.8-2.4 Hz, 1H, 4), 6.66-6.64 (d, J=8.4 Hz, 1H, 3), 6.09 (s, 2H, NH ). 3 2

MS (ES) m/z 276 (M+H+), 198, 105.

255

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Rx-ID: 44524133 Find similar reactions

42%

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With trifluorormethanesulfonic acid; tri(methylsalicyl)phosphate ester

T=20°C; 0.333333 h; chemoselective reaction;

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Sumita, Akinari; Otani, Yuko; Ohwada, Tomohiko

Chemical Communications, 2017 , vol. 53, # 9 p. 1482 - 1485 Title/Abstract Full Text View citing articles Show Details

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256

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A: 1%

Grimshaw, James; Silva, A. Prasanna de

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1982 , p. 857 - 866 Title/Abstract Full Text View citing articles Show Details

in cyclohexane

Irradiation;

257

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With hydrogenchloride

multistep reaction: acid hydrolysis, photolysis;

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Schutz; Fitz

Arzneimittel-Forschung/Drug Research, 1982 , vol. 32, # 3 p. 177 - 183 Title/Abstract Full Text View citing articles Show Details

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258

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With hydrogenchloride in methanol

T=70°C; 360 h; Further byproducts given;

Nudelman; De Waisbaum

Journal of Pharmaceutical Sciences, 1995 , vol. 84, # 8 p. 998 - 1004 Title/Abstract Full Text View citing articles Show Details

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259

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With hydrogenchloride in methanol

T=70°C; 360 h; Further byproducts given;

Nudelman; De Waisbaum

Journal of Pharmaceutical Sciences, 1995 , vol. 84, # 8 p. 998 - 1004 Title/Abstract Full Text View citing articles Show Details

With hydrogenchloride in methanol; water

T=80°C; 600 h;

Cabrera, C. Gallardo; Goldberg De Waisbaum; Nudelman, N. Sbarbati

Journal of Physical Organic Chemistry, 2005 , vol. 18, # 2 p. 156 - 161 Title/Abstract Full Text View citing articles Show Details

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260

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With hydrogenchloride in methanol

T=70°C; 360 h; Further byproducts given;

Nudelman; De Waisbaum

Journal of Pharmaceutical Sciences, 1995 , vol. 84, # 8 p. 998 - 1004 Title/Abstract Full Text View citing articles Show Details

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261

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With hydrogenchloride in methanol; water

T=50°C; 360 h; Product distribution;

Nudelman; De Waisbaum

Journal of Pharmaceutical Sciences, 1995 , vol. 84, # 2 p. 208 - 211 Title/Abstract Full Text View citing articles Show Details

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262

Synthesize Find similar Rx-ID: 3779084 Find similar reactions

With hydrogenchloride

multistep reaction: acid hydrolysis, photolysis;

Schutz; Fitz

Arzneimittel-Forschung/Drug Research, 1982 , vol. 32, # 3 p. 177 - 183 Title/Abstract Full Text View citing articles Show Details

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263

Synthesize Find similar Rx-ID: 3849512 Find similar reactions

With hydrogenchloride

multistep reaction: acid hydrolysis, photolysis;

Schutz; Fitz

Arzneimittel-Forschung/Drug Research, 1982 , vol. 32, # 3 p. 177 - 183 Title/Abstract Full Text View citing articles Show Details

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264

Synthesize Find similar Rx-ID: 3779524 Find similar reactions

With hydrogenchloride

multistep reaction: biotransformation, acid hydrolysis;

Schutz; Fitz

Arzneimittel-Forschung/Drug Research, 1982 , vol. 32, # 3 p. 177 - 183 Title/Abstract Full Text View citing articles Show Details

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265

Synthesize Find similar Rx-ID: 3229030 Find similar reactions

Schleuder; Richter; Keckeis; Jira

Pharmazie, 1993 , vol. 48, # 1 p. 33 - 37 Title/Abstract Full Text View citing articles Show Details

in water

T=121°C; 0.2 h; other temperatures and time; Product distribution;

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266

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Schleuder; Richter; Keckeis; Jira

Pharmazie, 1993 , vol. 48, # 1 p. 33 - 37 Title/Abstract Full Text View citing articles Show Details

in water

T=80°C; Product distribution;

267

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Rx-ID: 7370274 Find similar reactions

o-Fluorbenzoylchlorid, p-Bromanilin;

Hoffmann-La Roche

Patent: CH414652 , 1959 ; Chem.Abstr., 1968 , vol. 68, # 69054s Full Text Show Details

p-Brom-anilin, o-Fluorbenzoylchlorid;

Reeder; Sternbach

Patent: US3239564 , 1960 ; Chem.Abstr., 1966 , vol. 64, # 19498a Full Text Show Details

2-Fluor-benzoylchlorid 1) Erhitzen mit 4-Brom-anilin u. ZnCl2 2) Hydrolysem.wss. H2SO4;

Sternbach et al.

Journal of Organic Chemistry, 1962 , vol. 27, p. 3781,3782, 3786 Full Text View citing articles Show Details

Hide Details

2-Fluor-benzoylchlorid, 4-Bromanilin, ZnCl2;

Reeder; Sternbach

Patent: US3136815 , 1960 ; Chem.Abstr., 1964 , vol. 61, # 9515f Full Text Show Details

2-Fluor-benzoylchlorid, 1.)4-Brom-anilin, ZnCl2; 2.) H2SO4;

Hoffmann-LaRoche

Patent: DE1136709 , 1962 ; Chem.Abstr., 1963 , vol. 59, # 12827 Full Text Show Details

o-Fluorbenzoylchlorid, 1) p-Bromanilin, ZnCl2, 2) H2SO4;

Hoffmann-La Roche

Patent: DE1145626 , 1963 ; Chem.Abstr., 1964 , vol. 60, # 12033h Full Text Show Details

o-Fluorbenzoylchlorid 1) Bromanilin, ZnCl2 2) saure Hydrolyse;

F.Hoffmann La Roche and Co AG

Patent: CH414652US3427304 , 1966 ; Full Text Show Details

268

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Rx-ID: 24512646 Find similar reactions

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With hydrogenchloride; sulfuric acid; Zinc chloride in acetic acid; toluene

Hide Experimental Procedure

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Walser; Armin; Guidotti; Alessandro; Costa; Erminio

Patent: US5317018 A1, 1994 ; Title/Abstract Full Text Show Details

1:(2-Amino-5-fluorophenyl)(2-bromophenyl)methanone

EXAMPLE 1 (2-Amino-5-fluorophenyl)(2-bromophenyl)methanone A mixture of 20 g (0.15 mol) of zinc chloride and 50 g (0.23 mol) of 2-bromobenzoyl chloride was heated to 110° C. 4-Fluoroaniline, 13 g (0.12 mol) Was added over a period of 2 minutes, raising the temperature of the mixture to 160° C. This mixture was then heated and stirred for 3 hours at 210°-220° C. After cooling to 140° C., 200 mL of hot 3N hydrochloric acid was added cautiously. The mixture was stirred and heated to reflux for 5 minutes and the aqueous phase was decanted from the residue. This procedure was repeated twice. The residue was dissolved in 200 mL acetic acid and treated with 100 mL of 3N hydrochloric acid and 10 mL of concentrated sulfuric acid to form a mixture. This mixture was heated to reflux with stirring for 48 hours and then poured over ice and extracted with ether. The resulting ether extracts were washed with 2N sodium hydroxide solution, dried and evaporated. The residue was chromatographed over 300 g of silica gel using toluene. The fractions containing a yellow product were combined and evaporated to leave 12.6 g of yellow resin having the above formula. For analysis, a sample of the yellow resin was crystallized from ether/hexane and recrystallized from ethanol/hexane to give yellow crystals with m.p. 64°-66° C. A

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269

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A: 52% B: 18%

With aluminium trichloride

T=60 - 65°C; 0.75 h;

Misra, B. K.; Rao, Y. R.; Mahapatra, S. N.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1983 , vol. 22, # 11 p. 1132 - 1138 Title/Abstract Full Text Show Details

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270

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B: 37%

With hydrogenchloride

0.5 h; Heatingreflux;

Schleuder, M.; Butzki, Susanne; Richter, P.; Sokolov, A.

Pharmazie, 1987 , vol. 42, # 1 p. 54 - 55 Title/Abstract Full Text Show Details

With hydrogenchloride

Heatinghydrolysis; Product distribution;

Schleuder, M.; Butzki, Susanne; Richter, P.; Sokolov, A.

Pharmazie, 1987 , vol. 42, # 1 p. 54 - 55 Title/Abstract Full Text Show Details

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271

Synthesize Find similar Rx-ID: 6216962 Find similar reactions

A: 41.5 % Spectr.

272

With hydrogenchloride

10 h; Heating;

Schleuder; Butzki; Richter

Pharmazie, 1984 , vol. 39, # 7 p. 505 - 506 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 1182575 Find similar reactions

37%

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WISYS TECHNOLOGY FOUNDATION, INC.

Patent: WO2003/82832 A2, 2003 ; Location in patent: Page/Page column 49; 50-51 ;

Stage #1: T=0 - 120°C; 1 h; Stage #2: With zinc(II) chloride

T=120 - 195°C; 3 h; Stage #3: With hydrogenchloride; sulfuric acid; water

more than 3 stages; Hide Experimental Procedure

Title/Abstract Full Text Show Details

2-Amino-5-bromo-2'-chlorobenzophenone 19. 9 2-Chlorobenzoyl chloride (177 mL, 1.4 mol) was cooled in a 2-L flask equipped with a condenser and a thermometer to 0°C with an ice-water bath and 4-bromoaniline (100 g, 0.58 mol) was added to the cooled solution. The mixture was heated to 120°C and kept at this temperature for 1 h until analysis by TLC indicated 4-bromoaniline had been consumed (EtOAc: hexane, 1: 4). The solution was heated to 160°C and anhydrous ZnCl2 (95 g, 0.70 mol, flamed dried) was added in one portion. The temperature was increased to 195°C and stirring was maintained at this temperature for 3hr until no more bubbles were evolved. The mixture was cooled to 120°C and aq HC1 (12percent, 350 mL) was added dropwise slowly. The mixture was kept at reflux for 20 min, after which the aq layer was poured off. This procedure with aq HCl was repeated 4 times. Water (350 mL) was then added, and the mixture held at reflux for 20 min and then the water was poured off. This was repeated several times until the solid was not a block any more. Then H2SO4 (72percent, 700 mL) was added to the residue and the mixture was heated to reflux for about lhr until the reaction mixture became a homogeneous dark colored solution. The hot acidic solution was poured into a mixture of ice and water with stirring. The precipitate which resulted was filtered and washed with a large amount of cold water until the pH value of the solid was about 6. The solid was then suspended in ice water and aq NaOH (40percent, 290 mL) was added carefully. The mixture which resulted was stirred for 2 hrs. The solid was filtered and washed with ice water. The suspension of the solid in ice water was adjusted carefully to approximately pH=3 with aq H2S04 (40percent) dropwise. The solid which remained was filtered and washed with water to neutrality. The yellow solid 19 (66. 1 g, 37.0percent) was dried and used directly in the next step without further purification. 1H NMR (300 MHz, CDC13) 8 6.49 (s, br, 2H), 6.65 (d, 1H, J=8. 82 Hz), 7.26-7. 8 (m, 6H).

Bogatskii,A.V. et al.

Pharmaceutical Chemistry Journal, 1977 , vol. 11, # 11 p. 1520 - 1525 Khimiko-Farmatsevticheskii Zhurnal, 1977 , vol. 11, # 11 p. 85 - 91 Full Text View citing articles Show Details

(i) ZnCl2, (ii) aq. HCl, (iii) H2SO4; Multistep reaction;

273

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Rx-ID: 1204018 Find similar reactions

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Bogatskii,A.V. et al.

Pharmaceutical Chemistry Journal, 1977 , vol. 11, # 11 p. 1520 - 1525 Khimiko-Farmatsevticheskii Zhurnal, 1977 , vol. 11, # 11 p. 85 - 91 Full Text View citing articles Show Details

(i) ZnCl2, (ii) aq. HCl, (iii) H2SO4; Multistep reaction;

274

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With hydrogenchloride

0.5 h; boiling water bath;

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Rx-ID: 3699844 Find similar reactions

Golovenko, N. Ya.; Zin'kovskii, V. G.; Bogatskii, A. V.; Sharbatyan, P. A.; Andronati, S. A.

Pharmaceutical Chemistry Journal, 1980 , vol. 14, # 4 p. 208 - 213 Khimiko-Farmatsevticheskii Zhurnal, 1980 , vol. 14, # 4 p. 15 - 21 Title/Abstract Full Text View citing articles Show Details

275

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With hydrogenchloride

0.5 h; boiling water bath;

Rx-ID: 3848388 Find similar reactions

Golovenko, N. Ya.; Zin'kovskii, V. G.; Bogatskii, A. V.; Sharbatyan, P. A.; Andronati, S. A.

Pharmaceutical Chemistry Journal, 1980 , vol. 14, # 4 p. 208 - 213 Khimiko-Farmatsevticheskii Zhurnal, 1980 , vol. 14, # 4 p. 15 - 21 Title/Abstract Full Text View citing articles Show Details

276

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Rx-ID: 5972492 Find similar reactions

Bogatskii et al.

Voprosy Stereokhimii, 1977 , vol. 6, p. 74 Chem.Abstr., 1979 , vol. 90, # 168556 Full Text Show Details

277

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Rx-ID: 8997317 Find similar reactions

in tetrahydrofuran

T=20°C;

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Miki, Takashi; Kori, Masakuni; Mabuchi, Hiroshi; Banno, Hiroshi; Tozawa, Ryu-ichi; Nakamura, Masahira; Itokawa, Shigekazu; Sugiyama, Yasuo; Yukimasa, Hidefumi

Bioorganic and Medicinal Chemistry, 2002 , vol. 10, # 2 p. 401 - 414 Title/Abstract Full Text View citing articles Show Details

278

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Rx-ID: 3377009 Find similar reactions

With aluminium trichloride; triethylamine

1.) 25 deg C, 2.) 8-10 deg C, 10 min; Yield given. Multistep reaction. Yields of byproduct given;

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Acharya, Baman Prasad; Rao, Y. Ramachandra

Journal of Chemical Research, Miniprint, 1987 , # 4 p. 1001 - 1035 Title/Abstract Full Text Show Details

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279

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With hydrogenchloride

multistep reaction: biotransformation, acid hydrolysis;

Schutz; Fitz

Arzneimittel-Forschung/Drug Research, 1982 , vol. 32, # 3 p. 177 - 183 Title/Abstract Full Text View citing articles Show Details

280

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70.6%

With iron; acetic acid

T=55°C; 0.5 h;

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Rx-ID: 3573048 Find similar reactions

Hester, Jackson B.; Ludens, James H.; Emmert, D. Edward; West, Bruce E.

Journal of Medicinal Chemistry, 1989 , vol. 32, # 6 p. 1157 - 1163 Title/Abstract Full Text View citing articles Show Details

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281

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Rx-ID: 9405826 Find similar reactions

59%

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Stage #1: in tetrahydrofuran; diethyl ether; cyclohexane

T=0°C; 2 h; Stage #2: With chloro-trimethyl-silane in tetrahydrofuran; diethyl ether; cyclohexane

T=0°C; Stage #3: With hydrogenchloride in tetrahydrofuran; diethyl ether; cyclohexane

T=20°C; 0.5 h;

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Anzini, Maurizio; Canullo, Laura; Braile, Carlo; Cappelli, Andrea; Gallelli, Andrea; Vomero, Salvatore; Menziani, M. Cristina; De Benedetti, Pier G.; Rizzo, Milena; Collina, Simona; Azzolina, Ornella; Sbacchi, Massimo; Ghelardini, Carla; Galeotti, Nicoletta

Journal of Medicinal Chemistry, 2003 , vol. 46, # 18 p. 3853 - 3864 Title/Abstract Full Text View citing articles Show Details

282

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Multi-step reaction with 2 steps 1: 75.2 percent / NaOH / methanol; tetrahydrofuran / 1 h / 20 - 25 °C 2: 70.6 percent / aq. AcOH, Fe powder / 0.5 h / 55 °C View Scheme

Rx-ID: 18977261 Find similar reactions

Hester, Jackson B.; Ludens, James H.; Emmert, D. Edward; West, Bruce E.

Journal of Medicinal Chemistry, 1989 , vol. 32, # 6 p. 1157 - 1163 Title/Abstract Full Text View citing articles Show Details

283

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Multi-step reaction with 2 steps 1: 75.2 percent / NaOH / methanol; tetrahydrofuran / 1 h / 20 - 25 °C 2: 70.6 percent / aq. AcOH, Fe powder / 0.5 h / 55 °C View Scheme

Rx-ID: 18988589 Find similar reactions

Hester, Jackson B.; Ludens, James H.; Emmert, D. Edward; West, Bruce E.

Journal of Medicinal Chemistry, 1989 , vol. 32, # 6 p. 1157 - 1163 Title/Abstract Full Text View citing articles Show Details

284

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Rx-ID: 23659306 Find similar reactions

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WISYS TECHNOLOGY FOUNDATION, INC.

Patent: US2006/3995 A1, 2006 ; Location in patent: Page/Page column 43 ;

Hide Experimental Procedure

Title/Abstract Full Text Show Details

2-Amino-5-iodo-benzophenone was prepared from p-iodonitrobenzene and phenylacetonitrile according to Hester J B, et al., (1989) J Med Chem 32:1157-1163

285

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Rx-ID: 29774515 Find similar reactions

WiSys Technology Foundation

Patent: US2010/261711 A1, 2010 ;

Hide Experimental Procedure

Title/Abstract Full Text Show Details

Procedure for XLi 350 and XLi 352:

2-Amino-5-iodo-benzophenone 58 was prepared from p-iodonitrobenzene and phenylacetonitrile according to the literature. 2-Amino-5-chloro-benzophenone 59 was commercially available from Acros.

286

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Rx-ID: 30819197 Find similar reactions

98%

With tert.-butylhydroperoxide; iodine in diethyl ether

T=80°C; 18 h;

Yan, Yizhe; Wang, Zhiyong

Chemical Communications, 2011 , vol. 47, # 33 p. 9513 - 9515 Title/Abstract Full Text View citing articles Show Details

60%

With hydrogenchloride; iodic acid; potassium iodide in methanol; water

T=20°C; Hide Experimental Procedure

Showa Denko K.K.

Patent: EP2508527 A1, 2012 ; Location in patent: Page/Page column 25-26 ; Title/Abstract Full Text Show Details

Example 7 Synthesis of iridium complex compound (3-f) [Show Image] Synthesis of compound (f1) In a mixed solvent of 20 ml of methanol and 100 ml of water, 20 ml of 1N-HCl was dropwise added to 4.0 g of aminobenzophenone, 2.2 g of potassium iodide and 1.4 g of iodic acid at room temperature with stirring. After the resulting mixture was allowed to stand for one night, 30 ml of chloroform was added to perform extraction. The extract was washed with a sodium sulfite aqueous solution and then further washed with water twice. The resulting solution was dried over magnesium sulfate and then filtered. The solvent was distilled away under reduced pressure. Then, 30 ml of methanol was added, and the mixture was heated. Thereafter, 3 ml of water was added to precipitate crystals. After filtration, the filter residue was washed with methanol and water to obtain a solid compound (f1). The yield was 4.0percent (60percent).

38%

With N-iodo-succinimide in diethyl ether; acetonitrile

18 h; regiospecific reaction;

Patterson, Stephen; Alphey, Magnus S.; Jones, Deuan C.; Shanks, Emma J.; Street, Ian P.; Frearson, Julie A.; Wyatt, Paul G.; Gilbert, Ian H.; Fairlamb, Alan H.

Journal of Medicinal Chemistry, 2011 , vol. 54, # 19 p. 6514 - 6530 Title/Abstract Full Text View citing articles Show Details

Hide Details

With Iodine monochloride in dichloromethane

T=-70 - 20°C; Hide Experimental Procedure

GLAXOSMITHKLINE LLC; CROWE, Miriam; DAUGAN, Alain, Claude-Marie; GOSMINI, Romain, Luc, Marie; GRIMES, Richard, Martin; MIRGUET, Olivier; MORDAUNT, Jacqueline, Elizabeth

Patent: WO2011/54844 A1, 2011 ; Location in patent: Page/Page column 85 ; Title/Abstract Full Text Show Details

82:

Intermediate 82 : (2-amino-5-iodophenyl)(phenyl)methanoneTo a solution of 2-aminobenzophenone (50g, 263 mmol) in anhydrous DCM (800ml_) at -70°C was added iodine monochloride (49.4g, 305 mmol, 1 .2 equiv.). The reaction mixture was stirred at -60°C for 5h, then overnight at RT. The resulting mixture was hydrolyzed with saturated aqueous Na2SC>4 and then extracted with DCM. The resulting solid was filtered to give the title compound which was used without further purification.

With Iodine monochloride in dichloromethane

T=-70 - -60°C; 5 h; Hide Experimental Procedure

Crowe, Miriam; Daugan, Alain Claude-Marie; Gosmini, Romain Luc Marie; Grimes, Richard Martin; Mirguet, Olivier; Mordaunt, Jacqueline Elizabeth

Patent: US2012/202799 A1, 2012 ; Location in patent: Page/Page column 45 ; Title/Abstract Full Text Show Details

Intermediate 82: (2-amino-5-iodophenyl)(phenyl)methanone

Intermediate 82: (2-amino-5-iodophenyl)(phenyl)methanone To a solution of 2-aminobenzophenone (50 g, 263 mmol) in anhydrous DCM (800 mL) at -70° C. was added iodine monochloride (49.4 g, 305 mmol, 1.2 equiv.). The reaction mixture was stirred at -60° C. for 5 h, then overnight at RT. The resulting mixture was hydrolyzed with saturated aqueous Na2SO4 and then extracted with DCM. The resulting solid was filtered to give the title compound which was used without further purification.

With iodine; silver sulfate in ethanol

T=20°C; 12 h; Hide Experimental Procedure

Chiarini, Marco; Del Vecchio, Luana; Marinelli, Fabio; Rossi, Leucio; Arcadi, Antonio

Synthesis (Germany), 2016 , vol. 48, # 18 art. no. SS-2016-E0249-FA, p. 3017 - 3030 Title/Abstract Full Text View citing articles Show Details

Selective Iodination of 2-Aminoacylbenzenes 1a–c; Typical Procedure

General procedure: (2-Amino-5-chlorophenyl)(phenyl)methanone (1b) (0.300 g, 1.29mmol), I2 (0.327 g, 1.29 mmol) and Ag2SO4 (0.402 g, 1.29 mmol) in EtOH (10 ml) were stirred for 12 h at r.t. After this time, the crude mixture was filtered to eliminate the precipitate of inorganic salt and then washed with sat. Na2S2O3 solution. The organic phase was separated,dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel(n-hexane) to give 1p. Yield: 0.444 g (94percent).

287

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Rx-ID: 31460272 Find similar reactions

Multi-step reaction with 2 steps 1: CuCl2*H2O; potassium carbonate / N,N-dimethyl-formamide / 24 h / 60 °C 2: tert.-butylhydroperoxide; iodine / diethyl ether / 18 h / 80 °C View Scheme

Yan, Yizhe; Wang, Zhiyong

Chemical Communications, 2011 , vol. 47, # 33 p. 9513 - 9515 Title/Abstract Full Text View citing articles Show Details

288

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Multi-step reaction with 3 steps 1: tetrahydrofuran; diethyl ether 2: CuCl2*H2O; potassium carbonate / N,N-dimethyl-formamide / 24 h / 60 °C 3: tert.-butylhydroperoxide; iodine / diethyl ether / 18 h / 80 °C View Scheme

Rx-ID: 31460372 Find similar reactions

Yan, Yizhe; Wang, Zhiyong

Chemical Communications, 2011 , vol. 47, # 33 p. 9513 - 9515 Title/Abstract Full Text View citing articles Show Details

289

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Multi-step reaction with 4 steps 1: hydrogenchloride; iron / ethanol; water / 2 h / 80 °C 2: tetrahydrofuran; diethyl ether 3: CuCl2*H2O; potassium carbonate / N,N-dimethyl-formamide / 24 h / 60 °C 4: tert.-butylhydroperoxide; iodine / diethyl ether / 18 h / 80 °C View Scheme

Rx-ID: 31460419 Find similar reactions

Yan, Yizhe; Wang, Zhiyong

Chemical Communications, 2011 , vol. 47, # 33 p. 9513 - 9515 Title/Abstract Full Text View citing articles Show Details

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290

Synthesize Find similar Rx-ID: 2168230

Find similar reactions

A: 15%

Grimshaw, James; Silva, A. Prasanna de

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1982 , p. 857 - 866 Title/Abstract Full Text View citing articles Show Details

in cyclohexane

Irradiation;

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291

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Rx-ID: 1581541 Find similar reactions

With aluminium trichloride

1) ethylene chloride, 1 h 2) ethylene chloride, 45 min; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

Acharya, Baman P.; Rao, Y. Ramachandra

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1987 , vol. 26, # 1-12 p. 1133 - 1139 Title/Abstract Full Text Show Details

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292

Synthesize Find similar Rx-ID: 2105043 Find similar reactions

With aluminium trichloride

1) ethylene chloride, 1 h 2) ethylene chloride, MeOH, 45 min; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

Acharya, Baman P.; Rao, Y. Ramachandra

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1987 , vol. 26, # 1-12 p. 1133 - 1139 Title/Abstract Full Text Show Details

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293

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Rx-ID: 28945676 Find similar reactions

Stage #1: 2-aminophenyl-phenylmethanone With tert-butylhypochlorite in dichloromethane

T=-70°C; 0.166667 h; Stage #2: 2-(methylthio)acetamide in tetrahydrofuran; dichloromethane

T=-70 - 0°C; Stage #3: With triethylamine in tetrahydrofuran; dichloromethane

T=0 - 20°C; Hide Experimental Procedure

Medichem, S.A.

Patent: US2009/312575 A1, 2009 ; Location in patent: Page/Page column 5 ; Title/Abstract Full Text Show Details

Comparative Example 2Preparation of 2-amino-3-benzoyl-α-(methylthio)benzeneacetamide (i.e. compound of formula IV).This example was carried out following the teachings of Preparation 7 of U.S. Pat. No. 4,313,949 in a larger scale than Comparative Example 1.To a cold solution (-70° C.) of 19.7 g (0.1 mol) of 2-aminobenzophenone in 300 mL of anhydrous dichloromethane, under inert atmosphere, was added a solution of 11.4 g of freshly prepared tert-butyl hypochlorite in 30 mL of anhydrous dichloromethane, followed after 10 minutes by the addition of a solution of 10.5 g (0.1 mol) of methylthioacetamide in 300 mL of anhydrous tetrahydrofuran. The temperature was maintained at or below -55° C. during these additions. After 1 h at -60° C., the mixture was allowed to warm to 0° C. and 11.2 g of triethylamine was added between 0 and 5° C. The reaction mixture was allowed to warm to ambient temperature and the yellow-orange solution was washed twice with 100 mL of water. The organic phase was dried over sodium sulphate and concentrated. The oily residue was treated with diethyl ether and the resulting solid was collected by filtration and dried to yield 10.2 g as a light yellow powder (Yield: 34percent).Analytical data: HPLC purity: 62percent; Chlorination by-products observed by HPLC: 2-amino-3-benzoyl-5-chloro-α-(methylthio)benzeneacetamide: 25.4percent; 2-amino-5-chlorobenzophenone: 7.8percent; 2-amino-3-chlorobenzophenone: 1.1percent.The foregoing shows that the purity of compound (IV) decreases with scale of the preparation. A

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294

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Rx-ID: 606639 Find similar reactions

T=100 - 180°C; spaeter auf 200-220grad und Kochen des Reaktionsproduktes mit alkoh.Salzsaeure je nach der Dauer der Hydrolyse;

Angel

Journal of the Chemical Society, 1912 , vol. 101, p. 516 Full Text Show Details

295

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With iodine cloride in dichloromethane

T=-60°C; 5 h;

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Rx-ID: 2107348 Find similar reactions

Walser; Flynn; Mason; Crowley; Maresca; Yaremko; O'Donnell

Journal of Medicinal Chemistry, 1991 , vol. 34, # 3 p. 1209 - 1221 Title/Abstract Full Text View citing articles Show Details

296

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Rx-ID: 7304378 Find similar reactions

Aus d. o-Aminobenzophenon +ICl;

Hoffmann - La Roche

Patent: DE2062927 , 1970 ; Chem.Abstr., 1972 , vol. 76, # 59670 Full Text Show Details

Aus d. o-Aminobenzophenon +I2/Na-Persulfat;

Hoffmann - La Roche

Patent: DE2062927 , 1970 ; Chem.Abstr., 1972 , vol. 76, # 59670 Full Text Show Details

F.Hoffmann-La Roche u. Co. AG Patent: DE2030669 , 1971 ; Chem.Abstr., vol. 74, # 88077 Full Text Show Details

2-Amino-2'-fluor-benzophenon, JCl;

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297

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A: 300 mg B: 190 mg

With hydrogenchloride in methanol

4 h; Heating;

Acharya, Baman P.; Rao, Y. Ramachandra

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1987 , vol. 26, # 1-12 p. 1133 - 1139 Title/Abstract Full Text Show Details