Reaxys
PubChem
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Reactions (21)
Yield
Substances (1)
Citations (23)
Conditions
References
1
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Rx-ID: 1650472 Find similar reactions
100%
With potassium carbonate in N,Ndimethyl-formamide
T=20°C; 2 h; Hide Experimental Procedure
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PHARMAKEA, INC.; ROWBOTTOM, Martin W.; HUTCHINSON, John Howard; LONERGAN, David
Patent: WO2016/144702 A1, 2016 ; Location in patent: Paragraph 00363 ; Title/Abstract Full Text Show Details
46.1:Step 1: 4-(benzyloxy)-1H-indole (2)
To a stirred solution of 1H-indol-4-ol 1 (3.2 g, 12.9 mmol) in DMF (17 mL) at RT, were added benzyl bromide (2.43 g, 14.2 mmol) and K2C03 (5.35 g, 38.7 mmol). The reaction mixture was stirred at RT for 1.5 h. Additional benzyl bromide (0.40 g, 2.33 mmol) was added and the mixture stirred at RT for 30 mm. The mixture was diluted with water (200 mL) and extracted with EtOAc (3 x 50 mL). The combined organic extracts were washed with brine (20 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude was purified (silica gel; eluting 0-60percent EtOAc/ hexanes) to afford compound 2 as an amber oil (2.88 g, 100percent). ‘HNIVIR (500 IVIHz, DMSO-d6): 11.08 (s, 1H), 7.20—7.55 (m, 5H), 6.93—7.10 (m, 3H), 6.58 (m, 1H), 6.48 (m, 1H), 5.19 (s, 2H). 95%
With potassium carbonate in acetone
20 h; Ambient temperature;
McCormick, Kevin D.; Kobayashi, Kazumi; Goldin, Stanley M.; Laxma Reddy; Meinwald, Jerrold
Tetrahedron, 1993 , vol. 49, # 48 p. 11155 - 11168 Title/Abstract Full Text View citing articles Show Details
94%
With potassium carbonate in acetone
72 h; Heating;
Smart, Brian P.; Oslund, Rob C.; Walsh, Laura A.; Gelb, Michael H.
Journal of Medicinal Chemistry, 2006 , vol. 49, # 10 p. 2858 - 2860
Title/Abstract Full Text View citing articles Show Details
41%
With potassium carbonate in acetone
12 h; Reflux; Hide Experimental Procedure
PHARMAKEA, INC.; ROWBOTTOM, Martin W.; HUTCHINSON, John Howard; CALDERON, Imelda
Patent: WO2016/144703 A1, 2016 ; Location in patent: Paragraph 00348 ; Title/Abstract Full Text Show Details
51.1:Step 1: 4-(Benzyloxy)-lH-indole (2)
To a stirred solution of lH-indol-4-ol 1 (1 g, 7.52 mmol) in acetone (50 mL) were added benzyl bromide (1.54 g, 8.95 mmol) and K2C03 (3.11 g, 22.56 mmol) at RT under inert atmosphere. The reaction mixture was heated to reflux temperature and stirred for 12 h. The mixture was diluted with water (60 mL) and extracted with EtOAc (2 x 60 mL). The combined organic extracts were washed with brine (20 mL), dried (Na2S04), filtered, and concentrated under reduced pressure. The crude was purified (silica gel; eluting 1-6percent EtOAc/ hexanes) to afford compound 2 (650 mg, 41percent) as colorless sticky solid. 1H MR (500 MHz, DMSO-i): δ 11.08 (br s, 1H), 7.49 (d, J= 7.5 Hz, 2H), 7.39 (t, J= 7.5 Hz, 2H), 7.34-7.29 (m, 1H), 7.21 (t, J = 2.6 Hz, 1H), 7.01-6.92 (m, 2H), 6.55 (d, J= 7.2 Hz, 1H), 6.45-6.43 (m, 1H), 5.20 (s, 2H); LC- MS: m/z 224.3 (M + H+). With potassium carbonate in acetone
Heating;
Shinada, Tetsuro; Miyachi, Miki; Itagaki, Yasuhiro; Naoki, Hideo; Yoshihara, Kazuo; Nakajima, Terumi
Tetrahedron Letters, 1996 , vol. 37, # 39 p. 7099 - 7102 Title/Abstract Full Text View citing articles Show Details
With potassium carbonate in acetone
36 h; RefluxInert atmosphere;
Pouwer, Rebecca H.; Deydier, Sophie M.; Le, Phuc Van; Schwartz, Brett D.; Franken, Nicole C.; Davis, Rohan A.; Coster, Mark J.; Charman, Susan A.; Edstein, Michael D.; Skinner-Adams, Tina S.; Andrews, Katherine T.; Jenkins, Ian D.; Quinn, Ronald J.
ACS Medicinal Chemistry Letters, 2014 , vol. 5, # 2 p. 178 - 182 Title/Abstract Full Text View citing articles Show Details
2
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With dmap; triethylamine in dichloromethane
T=20°C; Hide Experimental Procedure
Rx-ID: 5470260 Find similar reactions
YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM LTD; BAR ILAN UNIVERSITY; NUDELMAN, Abraham; WEINSTOCK-ROSIN, Marta
Patent: WO2013/150529 A2, 2013 ; Location in patent: Page/Page column 25; 29; 30; 43 ; Title/Abstract Full Text Show Details
1:
General procedure: Procedure B: Synthesis of carbamates. Method I: A carbamoyl chloride (15 mmol) was added to a solution of 4-, 5- or 6-hydroxyindole; or to 4-, 5-, 6- or 7-hydroxyindole-3-propanoic acid (or ester) (7.51 mmol) in dry CH2C12 (50 mL) containing NEt3 (9.01 mmol) and 4-DMAP (10percent mol). The mixture was stirred at room temperature for 24-72 h. Despite the use of 2 eq of carbamoyl chloride, starting phenolic material remained (determined by TLC analysis). The reaction was quenched by addition of water, and the mixture was extracted with CH2CI2. The organic layer was washed with 5percent NaHCC>3, brine, dried over MgS04 and evaporated to give the crude carbamates. The residual carbamates were purified either by chromatography, or by extraction with 2N NaOH and CH2CI2 (in order to remove traces of unreacted hydroxyindoles and carbamoyl chlorides), followed by elution of the organic phase through a plug of silica gel, which was washed with EtO Ac-Hex (1 : 1). The filtrate was evaporated and the residue was crystallized from CH2CI2 and hexane. lH-Indol-4-yl ethylmethylcarbamate, AN-651. Compound AN-651 was prepared from 4-hydroxyindole by procedure B, Method I, was isolated by chromatography eluted with EtOAc-hexane (1 :3 to 1 :2 to 1 : 1). It was also crystallized from EtOAc-hexane as white needle in 61 percent yield, mp 113- 115 °C. 1H-NMR (300 MHz, Acetone-d6) ppm δ 10.31 (bs, 1H, H-1), 7.25-7.27 (m, 2H, H-2+H-7), 7.07 (t, J = 7.2 Hz, 1H, H-6), 6.81 (d, J = 2.0 Hz, 1H, H-5), 6.41 (bs, 1H, H-3), 3.37-3.59 (m, 2H, H-l l), 3.18+2.99 (s, 3H, H-13), 1.18-1.31 (m, 3H, H12). 13C-NMR (75 MHz, Acetone-d6) ppm δ 154.75, 145.66, 139.02, 125.49, 122.85, 122.07, 112.25, 109.27, 99.30, 44.62, 28.78, 13.56, 12.72; MS (CI+) m/z 219.114 (MH+, 100.00), 218.109 (M, 31.30); HRMS calcd. for C12H15N2O2 (MH+, DCI+/CH4) 219.1134; found 219.1138; Anal. Calcd. for C12H14N2O2 (218.25 g/mol): C, 66.04; H, 6.47; N, 12.84. Found C, 65.698; H, 6.636; N, 12.728. Julia; Pascal
Chimica Therapeutica, 1970 , vol. 5, p. 279,280, 283 Full Text Show Details
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Neurogen Corporation
Patent: US5484944 A1, 1996 ; Title/Abstract Full Text Show Details
5:Example 5
A slurry of semicarbazone (17.64 g, 54 mmol), Raney Nickel (18 g of a 50percent aqueous slurry) in 1:1 tetrahydrofuran:methanol (145 mL) was heated to 55° C. Hydrazine monohydrate was added in four equal portions (2.7 mL each) at 0.5 h intervals. The mixture was cooled, then filtered through a small pad of silica gel using ether. The filtrate was dried over magnesium sulfate, filtered, concentrated in vacuo, and the residue purified by flash chromatography to afford 4-benzyloxy-1H-indole as a low melting solid.
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Neurogen Corporation
Patent: US5723462 A1, 1998 ; Title/Abstract Full Text Show Details
1.5:5.
A slurry of this semicarbazone (17.64 g, 54 mmol) and Raney nickel (18 g of a 50percent aqueous slurry) in 1:1 tetrahydrofuran:methanol (145 mL) was heated to 55° C. Hydrazine monohydrate was added in four equal portions (2.7 mL each) at 0.5 h intervals. The mixture was cooled, then filtered through a small pad of silica gel using ether. The filtrate was dried over magnesium sulfate, filtered, concentrated in vacuo, and the residue purified by flash chromatography to afford 4-benzyloxy-1H-indole as a low melting solid. A
B
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3
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A: 6% B: 88%
With hydrogen; 5 rhodium-oncharcoal; nickel(II) nitrate in tetrahydrofuran; water
T=20°C; 32 h; Hide Experimental Procedure
BANYU PHARMACEUTICAL CO., LTD.
Patent: EP1541582 A1, 2005 ; Location in patent: Page/Page column 38 ; Title/Abstract Full Text Show Details
37:
Following a procedure similar to Example 32, 3-benzyloxy-2-(2-pyrrolidinylvinyl)nitrobenzene as a starting material was reduced in the presence of 5 percent rhodium/carbon powder and as a metal compound, ferrous(II) acetate, nickel(II) nitrate or cobalt (III) acetylacetonate as the catalyst of the present invention. The results are shown in the following Table 4, and in the case where the reducing agent of the present invention was used, 4-benzyloxyindole was obtained in a higher yield and 4-hydroxyindole was byproduced in a lower yield, compared to Comparison Example 3. A: 5% B: 83%
With hydrogen; 5 rhodium-oncharcoal; iron(II) acetate in tetrahydrofuran
T=20°C; 31 h; Hide Experimental Procedure
BANYU PHARMACEUTICAL CO., LTD.
Patent: EP1541582 A1, 2005 ; Location in patent: Page/Page column 38 ; Title/Abstract Full Text Show Details
36:
Following a procedure similar to Example 32, 3-benzyloxy-2-(2-pyrrolidinylvinyl)nitrobenzene as a starting material was reduced in the presence of 5 percent rhodium/carbon powder and as a metal compound, ferrous(II) acetate, nickel(II) nitrate or cobalt (III) acetylacetonate as the catalyst of the present invention. The results are shown in the following Table 4, and in the case where the reducing agent of the present invention was used, 4-benzyloxyindole was obtained in a higher yield and 4-hydroxyindole was byproduced in a lower yield, compared to Comparison Example 3. A: 3% B: 80%
With hydrogen; 5 rhodium-oncharcoal; tris(acetylacetonato)cobalt in tetrahydrofuran
T=20°C; 38 h; Hide Experimental Procedure
BANYU PHARMACEUTICAL CO., LTD.
Patent: EP1541582 A1, 2005 ; Location in patent: Page/Page column 38 ; Title/Abstract Full Text Show Details
38:
Following a procedure similar to Example 32, 3-benzyloxy-2-(2-pyrrolidinylvinyl)nitrobenzene as a starting material was reduced in the presence of 5 percent rhodium/carbon powder and as a metal compound, ferrous(II) acetate, nickel(II) nitrate or cobalt (III) acetylacetonate as the catalyst of the present invention. The results are shown in the following Table 4, and in the case where the reducing agent of the present invention was used, 4-benzyloxyindole was obtained in a higher yield and 4-hydroxyindole was byproduced in a lower yield, compared to Comparison Example 3.
A: 38% B: 43%
With hydrogen; 5 rhodium-on-charcoal in tetrahydrofuran
T=20°C; 167 h; Hide Experimental Procedure
BANYU PHARMACEUTICAL CO., LTD.
Patent: EP1541582 A1, 2005 ; Location in patent: Page/Page column 38 ; Title/Abstract Full Text Show Details
3:
Following a procedure similar to Example 32, 3-benzyloxy-2-(2-pyrrolidinylvinyl)nitrobenzene as a starting material was reduced in the presence of 5 percent rhodium/carbon powder and as a metal compound, ferrous(II) acetate, nickel(II) nitrate or cobalt (III) acetylacetonate as the catalyst of the present invention. The results are shown in the following Table 4, and in the case where the reducing agent of the present invention was used, 4-benzyloxyindole was obtained in a higher yield and 4-hydroxyindole was byproduced in a lower yield, compared to Comparison Example 3. A: 6 % Chromat. B: 88 % Chromat.
With hydrogen; Rh on carbon; nickel(II) nitrate in tetrahydrofuran
T=20°C;
Akao, Atsushi; Sato, Kimihiko; Nonoyama, Nobuaki; Mase, Toshiaki; Yasuda, Nobuyoshi
Tetrahedron Letters, 2006 , vol. 47, # 6 p. 969 - 972 Title/Abstract Full Text View citing articles Show Details
A: 38 % Chromat. B: 43 % Chromat.
With hydrogen; Rh on carbon in tetrahydrofuran
T=20°C;
Akao, Atsushi; Sato, Kimihiko; Nonoyama, Nobuaki; Mase, Toshiaki; Yasuda, Nobuyoshi
Tetrahedron Letters, 2006 , vol. 47, # 6 p. 969 - 972 Title/Abstract Full Text View citing articles Show Details
4
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Rx-ID: 24728024 Find similar reactions
With hydrochlorid acid; hydrazine hydrate; nickel monoaluminide in tetrahydrofuran; Nmethylacetamide; methanol; ethanol; water
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Neurogen Corporation
Patent: US5750702 A1, 1998 ; Title/Abstract Full Text Show Details
Hide Experimental Procedure
1.5:5.
5. 4-Benzyloxy-1H-indole STR57 A solution of 2-nitro-6-benzyloxytoluene (13.0 g, 53 mmol) and tris(dimethylamino)methane (13.9 mL, 80 mmol) in dimethylformamide (30 mL) was heated at 115° C. under Nitrogen for 3 h. Upon cooling to ambient temperature, a solution of semicarbazide hydochloride (6.26 g, 56 mmol) and concentrated hydrochloric acid (4.8 mL) in water (70 mL) was added dropwise with vigorous stirring. Ethanol (25 mL) was added and the heterogeneous mixture stirred for 2 h. After cooling in an ice bath, the precipitate was filtered, rinsed with, in sequence, ice water, cold 50percent aqueous ethanol, cold ethanol, then ether and dried to give a semicarbazone. A slurry of this semicarbazone (17.64 g, 54 mmol), Raney nickel (18 g of a 50percent aqueous slurry) in 1:1 tetrahydrofuran:methanol (145 mL) was heated to 55° C. Hydrazine monohydrate was added in four equal portions (2.7 mL each) at 0.5 h intervals. The mixture was cooled, then filtered through a small pad of silica gel using ether. The filtrate was dried over magnesium sulfate, filtered, concentrated in vacuo, and the residue purified by flash chromatography to afford 4-benzyloxy-1H-indole as a low melting solid.
5
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With methanol; ammonium chloride; magnesium in tetrahydrofuran
5 h; Ambient temperature;
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Rx-ID: 4267718 Find similar reactions
Ishibashi; Akamatsu; Iriyama; Hanaoka; Tabata; Ikeda
Chemical and Pharmaceutical Bulletin, 1994 , vol. 42, # 2 p. 271 - 276 Title/Abstract Full Text View citing articles Show Details
6
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Rx-ID: 1818015 Find similar reactions
74%
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T=120°C; P=10 - 20 Torr; 2.5 h;
Brenneisen; Borner; Peter-Oesch; Schlunegger
Archiv der Pharmazie, 1988 , vol. 321, # 8 p. 487 - 489 Title/Abstract Full Text View citing articles Show Details
With iron; silica gel
1) 120 deg C, 4 h, under vacuum 2) 1 h reflux in toluene-acetic acid; Yield given. Multistep reaction;
Kawase, Masami; Sinhababu, Achintya K.; Borchardt, Ronald T.
Journal of Heterocyclic Chemistry, 1987 , vol. 24, p. 1499 - 1501 Title/Abstract Full Text Show Details
7
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Rx-ID: 19152576 Find similar reactions
Brenneisen; Borner; Peter-Oesch; Schlunegger
Archiv der Pharmazie, 1988 , vol. 321, # 8 p. 487 - 489 Title/Abstract Full Text View citing articles Show Details
View Scheme
8
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Rx-ID: 19161301 Find similar reactions
Brenneisen; Borner; Peter-Oesch; Schlunegger
Archiv der Pharmazie, 1988 , vol. 321, # 8 p. 487 - 489 Title/Abstract Full Text View citing articles Show Details
9
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With sodium tetrahydroborate in 1,4dioxane; water
2 h; Heating;
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Rx-ID: 2848158 Find similar reactions
Nimtz, Manfred; Haefelinger, Guenter
Liebigs Annalen der Chemie, 1987 , p. 765 - 770 Title/Abstract Full Text Show Details
10
Synthesize Find similar Multi-step reaction with 2 steps 1: 7 percent / BCl3, ZnCl2 / benzene / 0.5 h / Heating 2: 31 percent / NaBH4 / dioxane; H2O / 2 h / Heating View Scheme
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Liebigs Annalen der Chemie, 1987 , p. 765 - 770 Title/Abstract Full Text Show Details
Rx-ID: 20630638 Find similar reactions
11
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Rx-ID: 2606702 Find similar reactions
With nickel boride; hydrazine hydrate in ethanol
Heating;
Lloyd, David H.; Nicholas, David E.
Journal of Organic Chemistry, 1986 , vol. 51, # 22 p. 4294 - 4295 Title/Abstract Full Text View citing articles Show Details
With titanium(III) chloride; ammonium acetate in acetone
Yield given;
Lloyd, David H.; Nichols, David E.
Tetrahedron Letters, 1983 , vol. 24, # 42 p. 4561 - 4562 Title/Abstract Full Text View citing articles Show Details
12
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Rx-ID: 19804085 Find similar reactions
Multi-step reaction with 2 steps 1: 93 percent / 6 h / 110 °C 2: 90 percent / nickel boride, hydrazine hydrate / ethanol / Heating View Scheme
Lloyd, David H.; Nicholas, David E.
Journal of Organic Chemistry, 1986 , vol. 51, # 22 p. 4294 - 4295 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: dimethylformamide / 30 h / Heating 2: NH4OAc, aq. TiCl3 / methanol; H2O / 0.12 h / Ambient temperature View Scheme
Somei; Inoue; Tokutake; et al.
Chemical and Pharmaceutical Bulletin, 1981 , vol. 29, # 3 p. 726 - 738 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: dimethylformamide / 30 h / Heating 2: aq. TiCl3 / acetic acid; H2O / 0.25 h / Ambient temperature View Scheme
Somei; Inoue; Tokutake; et al.
Chemical and Pharmaceutical Bulletin, 1981 , vol. 29, # 3 p. 726 - 738 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 3 steps 1: dimethylformamide / 30 h / Heating 2: 83.6 percent / Silica gel (100-200 mesh) / CH2Cl2; H2O / 4 h / Ambient temperature
Somei; Inoue; Tokutake; et al.
Chemical and Pharmaceutical Bulletin, 1981 , vol. 29, # 3 p. 726 - 738 Title/Abstract Full Text View citing articles Show Details
3: 74.9 percent / NH4OAc, aq. TiCl3 / methanol / 0.12 h / Ambient temperature; Zn, NH4Cl, MeOH-H2O, Rt, 4 h View Scheme
Multi-step reaction with 3 steps 1: dimethylformamide / 30 h / Heating 2: 83.6 percent / Silica gel (100-200 mesh) / CH2Cl2; H2O / 4 h / Ambient temperature 3: 1.) aq. TiCl3; 2.) acetic anhydride / 1.) MeOH, 5 min; 2.) pyridine, Rt, 8 h View Scheme
Somei; Inoue; Tokutake; et al.
Chemical and Pharmaceutical Bulletin, 1981 , vol. 29, # 3 p. 726 - 738 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: 4 h / 110 °C 2: TiCl3, 4M NH4OAc / acetone View Scheme
Lloyd, David H.; Nichols, David E.
Tetrahedron Letters, 1983 , vol. 24, # 42 p. 4561 - 4562 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: potassium ethylate; diethyl ether; toluene / Behandeln des Reaktionsprodukts in wss. NaOH mit Na2S2O4
2: quinaldine; copper-powder / 245 - 250 °C View Scheme
Stoll et al.
Helvetica Chimica Acta, 1955 , vol. 38, p. 1452,1469 Full Text Show Details
13
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Rx-ID: 2888795 Find similar reactions
With pyrrolidine; hydrazine hydrate; nickel 1.) DMF, 125 deg C, 3 h; 2.) methanol, 5060 deg C, 3 h; Yield given. Multistep reaction;
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Repke; Ferguson
Journal of Heterocyclic Chemistry, 1982 , vol. 19, # 4 p. 845 - 848 Title/Abstract Full Text View citing articles Show Details
A
B
C
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14
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With titanium(III) chloride
1.) MeOH, 5 min; 2.) pyridine, Rt, 8 h; Yield given. Multistep reaction. Yields of byproduct given;
Somei; Inoue; Tokutake; et al.
Chemical and Pharmaceutical Bulletin, 1981 , vol. 29, # 3 p. 726 - 738 Title/Abstract Full Text View citing articles Show Details
15
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With titanium(III) chloride; ammonium acetate in methanol
0.116667 h; Ambient temperatureZn, NH4Cl, MeOH-H2O, Rt, 4 h;
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Rx-ID: 3136820 Find similar reactions
Somei; Inoue; Tokutake; et al.
Chemical and Pharmaceutical Bulletin, 1981 , vol. 29, # 3 p. 726 - 738 Title/Abstract Full Text View citing articles Show Details
A
B
C
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16
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With titanium(III) chloride; acetic anhydride
1.) MeOH, 5 min; 2.) pyridine, Rt, 8 h; Yield given. Multistep reaction. Yields of byproduct given;
Somei; Inoue; Tokutake; et al.
Chemical and Pharmaceutical Bulletin, 1981 , vol. 29, # 3 p. 726 - 738 Title/Abstract Full Text View citing articles Show Details
17
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Rx-ID: 3141949 Find similar reactions
With titanium(III) chloride; ammonium acetate in methanol; water
0.116667 h; Ambient temperature; Yield given;
Somei; Inoue; Tokutake; et al.
Chemical and Pharmaceutical Bulletin, 1981 , vol. 29, # 3 p. 726 - 738 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: 83.6 percent / Silica gel (100-200 mesh) / CH2Cl2; H2O / 4 h / Ambient temperature 2: 74.9 percent / NH4OAc, aq. TiCl3 / methanol / 0.12 h / Ambient temperature; Zn, NH4Cl, MeOH-H2O, Rt, 4 h View Scheme
Somei; Inoue; Tokutake; et al.
Chemical and Pharmaceutical Bulletin, 1981 , vol. 29, # 3 p. 726 - 738 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: 83.6 percent / Silica gel (100-200 mesh) / CH2Cl2; H2O / 4 h / Ambient temperature 2: 1.) aq. TiCl3; 2.) acetic anhydride / 1.) MeOH, 5 min; 2.) pyridine, Rt, 8 h View Scheme
Somei; Inoue; Tokutake; et al.
Chemical and Pharmaceutical Bulletin, 1981 , vol. 29, # 3 p. 726 - 738 Title/Abstract Full Text View citing articles Show Details
A
B
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18
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With titanium(III) chloride in water; acetic acid
0.25 h; Ambient temperature; Yield given. Yields of byproduct given;
Somei; Inoue; Tokutake; et al.
Chemical and Pharmaceutical Bulletin, 1981 , vol. 29, # 3 p. 726 - 738 Title/Abstract Full Text View citing articles Show Details
19
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71%
With iron(II) sulfate
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Heterocycles, 1981 , vol. 16, # 7 p. 1119 - 1124 Title/Abstract Full Text Show Details
Rx-ID: 3588464 Find similar reactions
20
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T=245 - 250°C;
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Rx-ID: 373972 Find similar reactions
Stoll et al.
Helvetica Chimica Acta, 1955 , vol. 38, p. 1452,1469 Full Text Show Details
21
Synthesize Find similar Multi-step reaction with 3 steps 1: ethanol 2: potassium ethylate; diethyl ether; toluene / Behandeln des Reaktionsprodukts in wss. NaOH mit Na2S2O4
3: quinaldine; copper-powder / 245 - 250 °C View Scheme
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Rx-ID: 22200431 Find similar reactions
Stoll et al.
Helvetica Chimica Acta, 1955 , vol. 38, p. 1452,1469 Full Text Show Details