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

Reaxys

PubChem

eMolecules

Reactions (329)

Yield

Substances (27)

Citations (284)

Conditions

References A

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Rx-ID: 100236 Find similar reactions

T=120°C;

v. Auwers; Jordan Chemische Berichte, 1924 , vol. 57, p. 807 Full Text Show Details

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Rx-ID: 100347 Find similar reactions

v. Auwers; Jordan Chemische Berichte, 1924 , vol. 57, p. 807 Full Text Show Details

T=120°C; im Rohr;

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Rx-ID: 133596 Find similar reactions

With aluminium trichloride

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Statham

Journal of the Chemical Society, 1951 , p. 213 Full Text View citing articles Show Details

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Rx-ID: 158965 Find similar reactions

With alkaline aqueous sodium hypochlorite solution

Hewett et al.

Journal of the Chemical Society, 1948 , p. 292,294 Full Text Show Details

With ammonia; KNH2; potassium nitrate

White; Bergstrom

Journal of Organic Chemistry, 1942 , vol. 7, p. 497,503 Full Text View citing articles Show Details

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With sodium hydroxide; sodium hypobromide

man versetzt die filtrierte Loesung mit Alkohol;

Rx-ID: 272818 Find similar reactions

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Kliegl

Chemische Berichte, 1909 , vol. 42, p. 591 Full Text View citing articles Show Details

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Rx-ID: 285443 Find similar reactions

durch Alkalischmelze;

Wittig; Kleiner; Conrad

Justus Liebigs Annalen der Chemie, 1929 , vol. 469, p. 11 Full Text View citing articles Show Details

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With paraffin

T=300°C;

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Graebe; Ullmann

Justus Liebigs Annalen der Chemie, 1896 , vol. 291, p. 16 Full Text View citing articles Show Details

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Rx-ID: 336178 Find similar reactions

With iron; acetic acid

Simpson et al.

Journal of the Chemical Society, 1945 , p. 646,655 Full Text View citing articles Show Details

With nickel; ethyl acetate

Hydrogenation;

Ruggli; Hegedues

Helvetica Chimica Acta, 1941 , vol. 24, p. 703,714 Full Text Show Details

With hydrogenchloride; tin; ethanol

Geigy, Koenigs

Chemische Berichte, 1885 , vol. 18, p. 2402 Full Text View citing articles Show Details

Hide Details

With hydrogenchloride; tin(ll) chloride

Gabriel; Stelzner

Chemische Berichte, 1896 , vol. 29, p. 1313 Full Text View citing articles Show Details

With sodium hydroxide; zinc

Carre

Annales de Chimie (Cachan, France), 1910 , vol. <8>19, p. 220 Bulletin de la Societe Chimique de France, 1909 , vol. <4>5, p. 121 Full Text Show Details

Carre

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1909 , vol. 148, p. 493 Bulletin de la Societe Chimique de France, 1909 , vol. <4>5, p. 284 Full Text Show Details

With tin(ll) chloride in ethyl acetate

2 h; Heating;

Kettler; Sakowski; Wiesner; Ortmann; Jomaa; Schlitzer, Martin

Pharmazie, 2005 , vol. 60, # 5 p. 323 - 327 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: 73 percent / hydroxylamine hydrochloride / ethanol; pyridine / 30 h / Heating 2: 17 percent / CO; pentamethylcyclopentadienyl dicarbonyl iron(II) dimer / dioxane / 75 h / 150 °C / 38000 Torr View Scheme

O'Dell, David K.; Nicholas, Kenneth M.

Heterocycles, 2004 , vol. 63, # 2 p. 373 - 382 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 338427 Find similar reactions

With phosphorus pentachloride; benzene

Behandeln mit Aluminiumchlorid und Erwaermen des Produkts mit konz. Schwefelsaeure;

Stoermer; Fincke

Chemische Berichte, 1909 , vol. 42, p. 3119 Full Text Show Details

Ullmann; Bleier

Chemische Berichte, 1902 , vol. 35, p. 4278 Full Text Show Details

Multi-step reaction with 3 steps 1: PCl5 / benzene / 0.5 h / 50 °C 2: AlCl3 / 4 h / 80 - 90 °C 3: 6.63 g / conc. H2SO4 / 0.25 h / 120 °C View Scheme

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

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Rx-ID: 373354 Find similar reactions

With chromium(VI) oxide; acetic acid

Behandeln des Reaktionsprodukts mit wss. Schwefelsaeure;

Koelsch

Journal of the American Chemical Society, 1944 , vol. 66, p. 1983 Full Text View citing articles Show Details

Ritchie

Journal and Proceedings of the Royal Society of New South Wales, 1946 , vol. 80, p. 33,40 Full Text View citing articles Show Details

With chromium(VI) oxide; acetic acid

Behandeln des Reaktionsprodukts mit aethanol. Kalilauge;

Koelsch

Journal of the American Chemical Society, 1944 , vol. 66, p. 1983 Full Text View citing articles Show Details

Ritchie

Journal and Proceedings of the Royal Society of New South Wales, 1946 , vol. 80, p. 33,40 Full Text View citing articles Show Details

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Rx-ID: 395572 Find similar reactions

86%

With hydrogenchloride in water

T=125°C; 3 h;

Szabo, Fruzsina; Simko, Daniel; Novak, Zoltan

RSC Advances, 2014 , vol. 4, # 8 p. 3883 - 3886 Title/Abstract Full Text View citing articles Show Details

With hydrogenchloride

Lothrop; Goodwin

Journal of the American Chemical Society, 1943 , vol. 65, p. 363,365 Full Text View citing articles Show Details

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Rx-ID: 407292 Find similar reactions

With potassium hydroxide; palladium on activated charcoal; Lindlar's catalyst

Hydrogenation;

Ruggli; Hegedues

Helvetica Chimica Acta, 1941 , vol. 24, p. 703,714 Full Text Show Details

Multi-step reaction with 3 steps 1: sulfuric acid 2: aqueous sulfuric acid; ethanol 3: palladium/calcium carbonate; methanol. KOH-solution / Hydrogenation View Scheme

Ruggli; Hegedues

Helvetica Chimica Acta, 1941 , vol. 24, p. 703,714 Full Text Show Details

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Rx-ID: 619345 Find similar reactions

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Freundler

Bulletin de la Societe Chimique de France, 1904 , vol. <3> 31, p. 618 Full Text View citing articles Show Details

T=220°C;

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Rx-ID: 667268 Find similar reactions

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Grammaticakis

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1952 , vol. 235, p. 546 Full Text Show Details

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Rx-ID: 676765 Find similar reactions

With aluminium trichloride; benzene

Erwaermen des Reaktionsprodukts mit Schwefelsaeure;

Simpson et al.

Journal of the Chemical Society, 1945 , p. 646,655 Full Text View citing articles Show Details

Scheifele; DeTar

Organic Syntheses, 1963 , vol. Coll. Vol. IV, p. 34,35 Full Text Show Details

Multi-step reaction with 2 steps 1: AlCl3 / 4 h / 80 - 90 °C 2: 6.63 g / conc. H2SO4 / 0.25 h / 120 °C View Scheme

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

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Rx-ID: 827431 Find similar reactions

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Grammaticakis

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1952 , vol. 235, p. 546 Full Text Show Details

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Synthesize Find similar Rx-ID: 1630999 Find similar reactions

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Syamala, M. S.; Rao, B. Nageswer; Ramamurthy, V.

Tetrahedron, 1988 , vol. 44, # 23 p. 7234 - 7242 Title/Abstract Full Text View citing articles Show Details

Irradiationvarious solvents; with/without β-cyclodextrin; Product distribution;

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Synthesize Find similar Rx-ID: 1631000 Find similar reactions

Chenevert, Robert; Plante, Raaymond

Canadian Journal of Chemistry, 1983 , vol. 61, p. 1092 - 1095 Title/Abstract Full Text Show Details

in ethanol

50 h; Irradiationother solvent and reagent; Product distribution;

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Synthesize Find similar Rx-ID: 1631001 Find similar reactions

A: 15% B: 80%

in water

Irradiationsodium dodecyl sulfate micelles;

Singh, A. K.; Raghuraman, T. S.

Synthetic Communications, 1986 , vol. 16, # 4 p. 485 - 490 Title/Abstract Full Text Show Details

in methanol

T=20 - 25°C; 48 h; Irradiation; Yield given;

Magdy, M.; Malik, Abdel-; Mayo, Paul de

Canadian Journal of Chemistry, 1984 , vol. 62, p. 1275 - 1278 Title/Abstract Full Text Show Details

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82%

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With zirconium(IV) oxychloride

T=160 - 180°C; 0.5 h;

Rx-ID: 1631014 Find similar reactions

Ravi, Subban; Saravanan, Nagusamy; Shanthi, Andy; Dharmaraj, Nallusamy; Lakshmanan, Akoni J

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1991 , vol. 30, # 4 p. 443 - 445 Title/Abstract Full Text Show Details

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Rx-ID: 1710777 Find similar reactions

70%

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With n-butyllithium in tetrahydrofuran; hexane

T=-78°C; 0.333333 h; other reagent: tert-BuLi; other reaction Temperature: -100 deg C;

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Frye, Stephen V.; Johnson, Marty C.; Valvano, Nicole L.

Journal of Organic Chemistry, 1991 , vol. 56, # 11 p. 3750 - 3752 Title/Abstract Full Text View citing articles Show Details

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88.2%

With sulfuric acid

0.25 h; Ambient temperature;

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Rx-ID: 2570982 Find similar reactions

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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With hydrogenchloride in methanol; ethanol

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Rx-ID: 2993039 Find similar reactions

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

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With hydrogenchloride in methanol; ethanol

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Rx-ID: 2994086 Find similar reactions

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

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96.6%

With sulfuric acid

0.25 h; Ambient temperature;

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Rx-ID: 3664794 Find similar reactions

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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Rx-ID: 4861456 Find similar reactions

26%

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With palladium diacetate; caesium carbonate; triphenylphosphine in N,N-dimethyl-formamide

T=140°C;

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Inoh, Jun-Ichi; Satoh, Tetsuya; Pivsa-Art, Sommai; Miura, Masahiro; Nomura, Masakatsu

Tetrahedron Letters, 1998 , vol. 39, # 26 p. 4673 - 4676 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 4959367 Find similar reactions

95%

With potassium carbonate; dimethyl sulfate in acetonitrile

Heating;

Kamal, Ahmed; Arifuddin; Rao, N. Venugopal

Synthetic Communications, 1998 , vol. 28, # 21 p. 3927 - 3931 Title/Abstract Full Text View citing articles Show Details

92%

With triethylene diamine nickel thiosulfate; water in chloroform

T=20°C; Hydrolysis; 0.166667 h;

Kamal; Arifuddin; Rao

Synlett, 2000 , # 10 p. 1482 - 1484 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 5332945 Find similar reactions

54.6%

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Stage #1: With boron trichloride in tetrachloroethane, 1,1,2,2-

Sugasawa reaction; Cooling with iceReflux; Stage #2: With hydrogenchloride; water in tetrachloroethane, 1,1,2,2-

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Jiang, Peng; Zhao, Dong-Dong; Yang, Xiao-Li; Zhu, Xiao-Lin; Chang, Jin; Zhu, Hong-Jun

Organic and Biomolecular Chemistry, 2012 , vol. 10, # 24 p. 4704 - 4711 Title/Abstract Full Text View citing articles Show Details

T=80°C; Sugasawa reaction; 1 h; Cooling with ice;

With aluminium trichloride; boron trichloride in 1,2-dichloroethane

Acylation;

Pascal, Yves; Andrianjara, Charles R.; Auclair, Eric; Avenel, Nadine; Bertin, Bernadette; Calvet, Alain; Feru, Frederic; Lardon, Sophie; Moodley, Indres; Ouagued, Malika; Payne, Adrian; Pruniaux, Marie-Pierre; Szilagyi, Corinne

Bioorganic and Medicinal Chemistry Letters, 2000 , vol. 10, # 1 p. 35 - 38 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 5698863 Find similar reactions

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v. Auwers

Chemische Berichte, 1924 , vol. 57, p. 1730 Full Text View citing articles Show Details

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Rx-ID: 5698864 Find similar reactions

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v. Auwers

Chemische Berichte, 1924 , vol. 57, p. 1730 Full Text View citing articles Show Details

Rx-ID: 5698865

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Sondheimer

Chemische Berichte, 1896 , vol. 29, p. 1273 Full Text View citing articles Show Details

T=160°C; im Rohr;

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Rx-ID: 5698866 Find similar reactions

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Bruce

Journal of the Chemical Society, 1959 , p. 2366,2368 Full Text View citing articles Show Details

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Rx-ID: 5698867 Find similar reactions

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Statham

Journal of the Chemical Society, 1951 , p. 213 Full Text View citing articles Show Details

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Rx-ID: 5698868 Find similar reactions

Wittig; Kleiner; Conrad

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Justus Liebigs Annalen der Chemie, 1929 , vol. 469, p. 11 Full Text View citing articles Show Details

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Rx-ID: 5698869 Find similar reactions

Graebe; Ullmann

Justus Liebigs Annalen der Chemie, 1896 , vol. 291, p. 16 Full Text View citing articles Show Details

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Rx-ID: 5698870 Find similar reactions

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White; Bergstrom

Journal of Organic Chemistry, 1942 , vol. 7, p. 497,503 Full Text View citing articles Show Details

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63%

Hide Experimental Procedure

Rx-ID: 6048045 Find similar reactions

Shionogi and Co., Ltd.

Patent: US4160784 A1, 1979 ; Title/Abstract Full Text Show Details

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1:EXAMPLE 1

EXAMPLE 1 To a solution of aniline (466 mg) in dichloroethane (5 ml), a solution of boron trichloride (640 mg) in dichloroethane (2.1 ml), benzonitrile (1 ml) and aluminum chloride (734 mg) are added under ice cooling, and the mixture is refluxed for 6 hours. After cooling, the mixture is mixed with 2 N hydrochloric acid (10 ml) and heated at 70° to 80° C. for 20 minutes to hydrolyze 2-(phenyliminomethyl) aniline and the extracted with methylene chloride. The methylene chloride layer is washed with dilute hydrochloric acid, evaporated to remove the solvent, and the residuary benzonitrile is evaporated under reduced pressure. The residue is recrystallized from methylene chloride/n-hexane to give 2-aminobenzophenone (619 mg) as crystals melting at 107° to 108° C. The yield is 63percent.

Jacquier,R. et al.

Bulletin de la Societe Chimique de France, 1970 , p. 2672 - 2678 Full Text View citing articles Show Details

Mills,B.; Schofield,K.

Journal of the Chemical Society, 1961 , p. 5558 - 5560 Full Text View citing articles Show Details

Suzuki,K. et al.

Journal of Organic Chemistry, 1961 , vol. 26, p. 2239 - 2242 Full Text View citing articles Show Details

Cadogan,J.I.G. et al.

Journal of the Chemical Society [Section] C: Organic, 1970 , p. 2437 - 2441 Full Text View citing articles Show Details

Aeberli; Houlihan

Journal of Organic Chemistry, 1968 , vol. 33, # 4 p. 1640 Full Text View citing articles Show Details

Bacon; Hamilton

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1974 , p. 1970 Full Text Show Details

BASF

Patent: FR2232534DE2400111 , 1974 ; Chem.Abstr., vol. 81, # 192884 Full Text Show Details

Kwon et al.

Yuki Gosei Kagaku Kyokaishi, 1973 , vol. 31, p. 328,329 Full Text Show Details

Higashino et al.

Chemical and Pharmaceutical Bulletin, 1972 , vol. 20, p. 1874,1876 Full Text Show Details

Hoffmann-La Roche

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

Hoffmann-LaRoche

Patent: DE1145625 , 1963 ; Chem.Abstr., vol. 59, # 10056 Full Text Show Details

Ghosal; Dutta

Indian Journal of Chemistry, 1970 , vol. 8, p. 687 Full Text Show Details

Misra et al.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1979 , vol. 18, p. 19 Full Text Show Details

Ghosal; Dutta

Indian Journal of Chemistry, 1969 , vol. 7, p. 135,139 Full Text Show Details

Upjohn Co., Kalamazoo, Mich.

Patent: US3634455 , 1972 ; Chem.Abstr., 1972 , vol. 76, # 113064 Full Text Show Details

Bhattacharyya et al.

Journal of the Indian Chemical Society, 1979 , vol. 56, p. 328 Full Text Show Details

Elad et al.

Journal of Organic Chemistry, 1965 , vol. 30, p. 3252,3253 Full Text Show Details

Charlesworth; Charleson

Canadian Journal of Chemistry, 1968 , vol. 46, p. 1843,1844 Full Text Show Details

Bunnet; Hrutfiord

Journal of Organic Chemistry, 1962 , vol. 27, p. 4152,4155 Full Text Show Details

Shionogi

Patent: DE2707102 , 1977 ; Chem.Abstr., vol. 87, # 184218 Full Text Show Details

Sandoz Inc.

Patent: US3428644 , 1965 ; Chem.Abstr., 1969 , vol. 70, # 77589b Full Text Show Details

Sugasawa et al.

Journal of the American Chemical Society, 1978 , vol. 100, p. 4842,4847 Full Text Show Details

Tertov et al.

Zhurnal Organicheskoi Khimii, 1974 , vol. 10, p. 2617,2634 Full Text Show Details

Sionogi seiyaku k.k.

Patent: JP52100434 , 1977 ;

Ref. Zh., Khim., 1978 , vol. 15, # O38P Full Text Show Details

Monsanto Company

Patent: US3965220 A1, 1976 ;

Hide Experimental Procedure

Title/Abstract Full Text Show Details

The following list of illustrative compounds is therefore to be read in the light of the above teachings. Aliphatic and Alicyclic Amines methylamine n-butylamine tetramethylammonium chloride ... 3-anilino-1-propanol 4-amino-1-naphthol amino acetophenone 2-phenylamino-3-butanone aminobenzophenone Hide Details

BASF Aktiengesellschaft

Patent: US4082749 A1, 1978 ;

Hide Experimental Procedure

Title/Abstract Full Text Show Details

4:EXAMPLE 4

EXAMPLE 4 45 parts of the amide of benzophenone-o-carboxylic acid is introduced into a solution of 10 parts of sodium hydroxide in 150 parts by volume of water. 0.5 part of sulfamic acid and then slowly 110 parts of hypochlorite solution (containing 15.4 parts of sodium hypochlorite are added to the suspension at 20° C while stirring. A clear solution is formed. It is heated to 80° C whereupon the amine is precipitated. The mixture is then heated for half an hour at 100° C, cooled and suction filtered at ambient temperature. The yield is 38.6 parts (97.9percent of theory) of o-aminobenzophenone having a melting point of 97° to 104° C.

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Rx-ID: 7448303 Find similar reactions

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Stoermer; Fincke

Chemische Berichte, 1909 , vol. 42, p. 3119 Full Text Show Details

Ullmann; Bleier

Chemische Berichte, 1902 , vol. 35, p. 4278 Full Text Show Details

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Rx-ID: 8679811 Find similar reactions

94%

With ammonia; iron(II) sulfate in methanol; water

T=20°C; Reduction; 2.5 h;

Kamal; Laxman; Arifuddin

Tetrahedron Letters, 2000 , vol. 41, # 40 p. 7743 - 7746 Title/Abstract Full Text View citing articles Show Details

70%

With methanol; sodium sulfide

0.166667 h;

Kazemi, Foad; Kiasat, Ali Reza; Sayyahi, Sohyl

Phosphorus, Sulfur and Silicon and the Related Elements, 2004 , vol. 179, # 9 p. 1813 - 1817 Title/Abstract Full Text View citing articles Show Details

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Stage #1: With polystyrene Rink amine resin; 2,2'-bis(diphenylphosphino)-1,1'- binaphthyl; sodium t-butanolate; tris(dibenzylideneacetone)dipalladium(0) in 1,4-dioxane; tert-butyl alcohol

T=80°C; 20 h; Stage #2: in dichloromethane

0.75 h; Further stages.;

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Rx-ID: 9247701 Find similar reactions

Weigand, Klaus; Pelka, Sylvie

Organic Letters, 2002 , vol. 4, # 26 p. 4689 - 4692 Title/Abstract Full Text View citing articles Show Details

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100%

Stage #1: With sulfuric acid

T=0 - 20°C; 2 h; Inert atmosphereSchlenk technique; Stage #2: With sodium hydrogencarbonate

Inert atmosphereSchlenk technique;

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Rx-ID: 9313232 Find similar reactions

Bhanuchandra; Ramu Yadav; Rit, Raja K.; Rao Kuram, Malleswara; Sahoo, Akhila K.

Chemical Communications, 2013 , vol. 49, # 45 p. 5225 - 5227 Title/Abstract Full Text View citing articles Show Details

6.63 g

With sulfuric acid

T=120°C; 0.25 h;

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

With sulfuric acid; water

T=120°C; 0.25 h; Hide Experimental Procedure

Guo, Zongru; Cheng, Guifang; Chu, Fengming

Patent: US2004/58977 A1, 2004 ; Location in patent: Page/Page column 14 ; Title/Abstract Full Text Show Details

Preparation of Substituted 2-Amino-benzophenone2 Example 8 2-Amino-benzophenone [0155] The mixture of 14.6 g (0.050 mol) of p-toluenesulfonylanthranilic acid prepared in Example 8 and 11.9 g (0.057 mol) of phosphorus pentachloride in 150 ml of dry benzene were heated at about 50° C. for 0.5 h. Cooled to 20-25° C. and 29.0 g (0.218 mol) of anhydrous aluminum chloride was added in portions. When addition was complete, the mixture was heated at 80-90° C. for 4 h and then cooled, poured onto a mixture of ice and 60 ml of 1N hydrochloride acid. The benzene was removed by vacuo distillation, the crude product was separated by filtration and washed with sodium carbonate and water. The filter cake is sucked reasonably dry, dissolved in 160 ml of conc. sulfuric acid and heated to 120° C. for 15 minutes. The reaction mixture was cooled and poured onto the mixture of ice and 1 g of norit, and the solution is filtered. The filtrate was neutralized with 12N ammonium hydroxide. The solid filtered off, washed with water and dried, recrystallized from 95percent ethanol to give the title compound (6.63 g) as yellow crystal, yield 65.0percent, m.p. 105-106° C. A

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With ammonium chloride; zinc in ethanol; water

T=20°C;

Howie; Jabbar, Abdul; Lewis, John R.; Nizami, Shaikh S.; Ritchie, Craig F.

Acta Crystallographica Section C: Crystal Structure Communications, 2003 , vol. 59, # 9 p. o516-o519 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 9524348 Find similar reactions

A: 83% B: 16%

With sodium hydride in tetrahydrofuran

2.5 h; Heating;

Park, Kwanghee Koh; Lee, Jin Joo

Tetrahedron, 2004 , vol. 60, # 13 p. 2993 - 2999 Title/Abstract Full Text View citing articles Show Details

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A: 62% B: 23%

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With sodium hydride in tetrahydrofuran

9 h; Heating;

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Park, Kwanghee Koh; Lee, Jin Joo

Tetrahedron, 2004 , vol. 60, # 13 p. 2993 - 2999 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 9553805 Find similar reactions

A: 52% B: 17%

With carbon monoxide; pentamethylcyclopentadienyl dicarbonyl iron(II) dimer in 1,4-dioxane

T=150°C; P=38000 Torr; 75 h;

O'Dell, David K.; Nicholas, Kenneth M.

Heterocycles, 2004 , vol. 63, # 2 p. 373 - 382 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 9558893 Find similar reactions

A: 22% B: 65%

With sodium hydride in tetrahydrofuran

20 h; Heating;

Park, Kwanghee Koh; Lee, Jin Joo

Tetrahedron, 2004 , vol. 60, # 13 p. 2993 - 2999 Title/Abstract Full Text View citing articles Show Details

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453 mg

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With sodium hydroxide; water in N,N-dimethyl-formamide

0.5 h; Heating;

Rx-ID: 9912616 Find similar reactions

Mizuno, Masahiro; Yamano, Mitsuhisa

Organic Letters, 2005 , vol. 7, # 17 p. 3629 - 3631 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 10214976 Find similar reactions

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88%

With trifluorormethanesulfonic acid; tri(methylsalicyl)phosphate ester

T=20°C; 0.333333 h; Reagent/catalyst; chemoselective reaction;

Sumita, Akinari; Otani, Yuko; Ohwada, Tomohiko

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

48%

With PPA in dichloromethane

T=80°C; Friedel-Crafts acylation; 2 h;

Ivanov, Iliyan; Nikolova, Stoyanka; Statkova-Abeghe, Stela

Synthetic Communications, 2006 , vol. 36, # 10 p. 1405 - 1411 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 10332540 Find similar reactions

93%

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

T=80°C; 36 h; Schlenk technique; Catalytic

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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

behavior; SolventReagent/catalyst;

31%

With [2,2']bipyridinyl; potassium fluoride; acetic acid; palladium diacetate in tetrahydrofuran

T=80°C; 48 h;

Zhao, Baowei; Lu, Xiyan

Tetrahedron Letters, 2006 , vol. 47, # 38 p. 6765 - 6768 Title/Abstract Full Text View citing articles Show Details

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99 % Chromat.

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Rx-ID: 10416087 Find similar reactions

Cadierno, Victorio; Garcia-Garrido, Sergio E.; Gimeno, Jose; Nebra, Noel

Chemical Communications, 2005 , # 32 p. 4086 - 4088 Title/Abstract Full Text View citing articles Show Details

With water; [{Ru(η3:η3-[-CH2C(CH3)=CHCH2]2)(μ-Cl)Cl}2]

T=90°C; 2 h;

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Rx-ID: 13864802 Find similar reactions

95%

With palladium on activated charcoal; hydrogen; acetic acid in methanol

T=20°C; P=760.051 Torr; 5 h;

Chen, Jia-Hua; Chen, Zi-Cong; Zhao, Hong; Zhang, Ting; Wang, Wei-Juan; Zou, Yong; Zhang, Xue-Jing; Yan, Ming

Organic and Biomolecular Chemistry, 2016 , vol. 14, # 17 p. 4071 - 4076 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 3 steps 1: 93 percent / MnO2 / CH2Cl2 / 20 h / Heating 2: 73 percent / hydroxylamine hydrochloride / ethanol; pyridine / 30 h / Heating 3: 17 percent / CO; pentamethylcyclopentadienyl dicarbonyl iron(II) dimer / dioxane / 75 h / 150 °C / 38000 Torr View Scheme

O'Dell, David K.; Nicholas, Kenneth M.

Heterocycles, 2004 , vol. 63, # 2 p. 373 - 382 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 4 steps 1: 68.7 percent / Na2CO3 / H2O / 60 - 85 °C 2: PCl5 / benzene / 0.5 h / 50 °C 3: AlCl3 / 4 h / 80 - 90 °C 4: 6.63 g / conc. H2SO4 / 0.25 h / 120 °C View Scheme

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Rx-ID: 14305735 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

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Multi-step reaction with 2 steps 1: 1.) 25 deg C, 45 min, 2.) diethyl ether, 1 h 2: 96.6 percent / conc. H2SO4 / 0.25 h / Ambient temperature View Scheme

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Rx-ID: 18563142 Find similar reactions

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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Multi-step reaction with 2 steps 1: 1.) 25 deg C, 45 min, 2.) diethyl ether, 1 h 2: 96.6 percent / conc. H2SO4 / 0.25 h / Ambient temperature View Scheme

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Rx-ID: 18596875 Find similar reactions

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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Multi-step reaction with 2 steps 1: cyclohexane / Irradiation 2: hydrochloric acid / methanol; ethanol View Scheme

Rx-ID: 20632817 Find similar reactions

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

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Multi-step reaction with 2 steps 1: cyclohexane / Irradiation 2: hydrochloric acid / methanol; ethanol View Scheme

Rx-ID: 20632893 Find similar reactions

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

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Multi-step reaction with 2 steps 1: 75 percent / triethylamine / aq. ethanol / 1.5 h / Heating 2: 70 percent / n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C / other reagent: tert-BuLi; other reaction Temperature: -100 deg C View Scheme

Rx-ID: 21591983 Find similar reactions

Frye, Stephen V.; Johnson, Marty C.; Valvano, Nicole L.

Journal of Organic Chemistry, 1991 , vol. 56, # 11 p. 3750 - 3752 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 22056838 Find similar reactions

Multi-step reaction with 2 steps 1: aqueous sulfuric acid; ethanol 2: palladium/calcium carbonate; methanol. KOH-solution / Hydrogenation View Scheme

Ruggli; Hegedues

Helvetica Chimica Acta, 1941 , vol. 24, p. 703,714 Full Text Show Details

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Multi-step reaction with 2 steps 1: sodium carbonate 2: benzene; phosphorus pentachloride / Behandeln mit Aluminiumchlorid und Erwaermen des Produkts mit konz. Schwefelsaeure View Scheme

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Rx-ID: 22063184 Find similar reactions

Ullmann; Bleier

Chemische Berichte, 1902 , vol. 35, p. 4278 Full Text Show Details

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Rx-ID: 22063476 Find similar reactions

Multi-step reaction with 2 steps 1: diethyl ether / Erhitzen des nach der Hydrolyse erhaltenen Reaktionsprodukts mit CrO3 in Essigsaeure 2: Raney nickel; ethyl acetate / Hydrogenation View Scheme

Ruggli; Hegedues

Helvetica Chimica Acta, 1941 , vol. 24, p. 703,714 Full Text Show Details

Multi-step reaction with 2 steps 1: benzene 2: aq.-ethanolic hydrochloric acid View Scheme

Lothrop; Goodwin

Journal of the American Chemical Society, 1943 , vol. 65, p. 363,365 Full Text View citing articles Show Details

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Rx-ID: 22070080 Find similar reactions

Multi-step reaction with 2 steps 1: diethyl ether / Erhitzen des nach der Hydrolyse erhaltenen Reaktionsprodukts mit CrO3 in Essigsaeure 2: Raney nickel; ethyl acetate / Hydrogenation View Scheme

Ruggli; Hegedues

Helvetica Chimica Acta, 1941 , vol. 24, p. 703,714 Full Text Show Details

Multi-step reaction with 5 steps 1: concentrated aqueous NaOH-solution 2: CHCl3; PCl5

3: AlCl3 / Behandeln des Reaktionsprodukts mit Wasser 4: CrO3; glacial acetic acid 5: alcohol; tin; hydrochloric acid View Scheme

Geigy, Koenigs

Chemische Berichte, 1885 , vol. 18, p. 2402 Full Text View citing articles Show Details

Multi-step reaction with 3 steps 1: hydrogenchloride; iron / ethanol; water / 2 h / 80 °C 2: tetrahydrofuran; diethyl ether 3: copper(II) chloride monohydrate; potassium carbonate / N,Ndimethyl-formamide / 24 h / 60 °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

Hide Details

Multi-step reaction with 2 steps 1: tetrahydrofuran / 1 h / -78 °C 2: palladium on activated charcoal; acetic acid; hydrogen / methanol / 5 h / 20 °C / 760.05 Torr View Scheme

Chen, Jia-Hua; Chen, Zi-Cong; Zhao, Hong; Zhang, Ting; Wang, Wei-Juan; Zou, Yong; Zhang, Xue-Jing; Yan, Ming

Organic and Biomolecular Chemistry, 2016 , vol. 14, # 17 p. 4071 - 4076 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: CrO3; glacial acetic acid 2: alcohol; tin; hydrochloric acid View Scheme

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Rx-ID: 22078930 Find similar reactions

Geigy, Koenigs

Chemische Berichte, 1885 , vol. 18, p. 2402 Full Text View citing articles Show Details

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Multi-step reaction with 4 steps 1: CHCl3; PCl5

2: AlCl3 / Behandeln des Reaktionsprodukts mit Wasser 3: CrO3; glacial acetic acid 4: alcohol; tin; hydrochloric acid View Scheme

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Rx-ID: 22084183 Find similar reactions

Geigy, Koenigs

Chemische Berichte, 1885 , vol. 18, p. 2402 Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 1: AlCl3 / Behandeln des Reaktionsprodukts mit Wasser 2: CrO3; glacial acetic acid 3: alcohol; tin; hydrochloric acid View Scheme

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Rx-ID: 22106217 Find similar reactions

Geigy, Koenigs

Chemische Berichte, 1885 , vol. 18, p. 2402 Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 1: AlCl3 / Behandeln des Reaktionsprodukts mit Wasser 2: CrO3; glacial acetic acid 3: alcohol; tin; hydrochloric acid View Scheme

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Rx-ID: 22113903 Find similar reactions

Geigy, Koenigs

Chemische Berichte, 1885 , vol. 18, p. 2402 Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: potassium acetate 2: chromium (VI)-oxide; acetic acid / Behandeln des Reaktionsprodukts mit aethanol. Kalilauge View Scheme

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Rx-ID: 22219454 Find similar reactions

Koelsch

Journal of the American Chemical Society, 1944 , vol. 66, p. 1983 Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 1: concentrated aqueous hydrochloric acid 2: potassium acetate 3: chromium (VI)-oxide; acetic acid / Behandeln des Reaktionsprodukts mit aethanol. Kalilauge View Scheme

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Rx-ID: 22230170 Find similar reactions

Koelsch

Journal of the American Chemical Society, 1944 , vol. 66, p. 1983 Full Text View citing articles Show Details

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Rx-ID: 22232800 Find similar reactions

Koelsch

Journal of the American Chemical Society, 1944 , vol. 66, p. 1983 Full Text View citing articles Show Details

Multi-step reaction with 3 steps 1: dodecanesulphonic acid sodium salt / water / 0.5 h / 20 °C 2: palladium diacetate; trifluoroacetic acid; tert.-butylhydroperoxide / water / 24 h / 20 °C 3: hydrogenchloride / water / 3 h / 125 °C View Scheme

Szabo, Fruzsina; Simko, Daniel; Novak, Zoltan

RSC Advances, 2014 , vol. 4, # 8 p. 3883 - 3886 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: benzene; ammonia 2: NaOH-solution; sodium hypobromite / man versetzt die filtrierte Loesung mit Alkohol View Scheme

Rx-ID: 22241872 Find similar reactions

Graebe; Ullmann

Justus Liebigs Annalen der Chemie, 1896 , vol. 291, p. 16 Full Text View citing articles Show Details

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Rx-ID: 30112796 Find similar reactions

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93%

Stage #1: 2-iodophenylamine; phenylboronic acid With potassium carbonate in toluene

Suzuki cross-coupling reaction; 0.166667 h; Autoclave; Stage #2: carbon monoxide in toluene

T=100°C; Suzuki cross-coupling reaction; P=5171.62 Torr; 10 h; Autoclave;

Qureshi, Ziyauddin S.; Deshmukh, Krishna M.; Tambade, Pawan J.; Bhanage, Bhalchandra M.

Synthesis, 2011 , # 2 art. no. P15410SS, p. 243 - 250 Title/Abstract Full Text View citing articles Show Details

89%

With potassium carbonate in methoxybenzene

T=80°C; carbonylative Suzuki-Miyaura crosscoupling; P=760.051 Torr; 12 h;

Cai, Mingzhong; Peng, Jian; Hao, Wenyan; Ding, Guodong

Green Chemistry, 2011 , vol. 13, # 1 p. 190 - 196 Title/Abstract Full Text View citing articles Show Details

84%

Stage #1: 2-iodophenylamine; phenylboronic acid With potassium carbonate in toluene

Suzuki Coupling; 0.166667 h; Autoclave; Stage #2: carbon monoxide in toluene

T=100°C; P=7500.75 Torr; 8 h;

Khedkar, Mayur V.; Sasaki, Takehiko; Bhanage, Bhalchandra M.

RSC Advances, 2013 , vol. 3, # 21 p. 7791 - 7797 Title/Abstract Full Text View citing articles Show Details

Hide Details

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83%

With 10 palladium on activated carbon; potassium carbonate in methoxybenzene

Khedkar, Mayur V.; Tambade, Pawan J.; Qureshi, Ziyauddin S.; Bhanage, Bhalchandra M.

European Journal of Organic Chemistry, 2010 , # 36 p. 6981 - 6986

T=100°C; Suzuki carbonylation; P=10343.2 Torr; 8 h; Autoclave;

Title/Abstract Full Text View citing articles Show Details

69%

With Bedford’s palladacycle; potassium carbonate; methoxybenzene

T=120°C; Suzuki-Miyaura Coupling; P=1500.15 Torr; 5 h; Autoclave;

Gautam, Prashant; Bhanage, Bhalchandra M.

Journal of Organic Chemistry, 2015 , vol. 80, # 15 p. 7810 - 7815 Title/Abstract Full Text View citing articles Show Details

39%

With potassium carbonate

T=100°C; Suzuki-Miyaura Coupling; P=1500.15 Torr; 6 h; Autoclave; Catalytic behavior;

Gautam, Prashant; Dhiman, Mahak; Polshettiwar, Vivek; Bhanage, Bhalchandra M.

Green Chemistry, 2016 , vol. 18, # 21 p. 5890 - 5899 Title/Abstract Full Text View citing articles Show Details

95 %Chromat.

With potassium carbonate

T=80°C; Suzuki Coupling; P=760.051 Torr; 12 h; Catalytic behavior;

Niu, Jianrui; Liu, Mengmeng; Wang, Peng; Long, Yu; Xie, Miao; Li, Rong; Ma, Jiantai

New Journal of Chemistry, 2014 , vol. 38, # 4 p. 1471 - 1476 Title/Abstract Full Text View citing articles Show Details

96 %Chromat.

With potassium carbonate

T=80°C; Suzuki Coupling; P=760.051 Torr; 12 h;

Zhu, Xiaohang; Niu, Jianrui; Zhang, Fengwei; Zhou, Jinghui; Li, Xinzhe; Ma, Jiantai

New Journal of Chemistry, 2014 , vol. 38, # 9 p. 4622 - 4627 Title/Abstract Full Text View citing articles Show Details

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50%

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Stage #1: With copper(l) iodide; glucosamine Hydrochloride; potassium carbonate in water; acetone

T=90°C; 0.166667 h; Stage #2: With ammonia in water; acetone

T=90°C; 30 h;

Rx-ID: 30741269 Find similar reactions

Thakur, Krishna Gopal; Ganapathy, Dhandapani; Sekar, Govindasamy

Chemical Communications, 2011 , vol. 47, # 17 p. 5076 - 5078 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 31031279 Find similar reactions

88%

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Stage #1: With trifluorormethanesulfonic acid in dichloromethane

T=60 - 80°C; Houben-Housch synthesis; Inert atmosphere; Stage #2: With water in dichloromethane

Houben-Housch synthesis; Inert atmosphereCooling with ice; Stage #3: With sodium hydroxide in water

Inert atmosphere; Hide Experimental Procedure

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Raja, Erum K.; Klumpp, Douglas A.

Tetrahedron, 2011 , vol. 67, # 25 p. 4494 - 4497 Title/Abstract Full Text View citing articles Show Details

4.2. General preparation of the ketones

General procedure: The amino-nitrile (1 mmol) is dissolved in dry CH2Cl2 (5 mL) to which is added benzene (2 mL). With stirring, triflic acid (2 mL) is then slowly added and the reaction mixture is stirred overnight at 60-80 °C. The mixture is then quenched by pouring the solution over ice/water. The aqueous solution is then made basic by slow addition of 10 M NaOH and the solution is extracted twice with chloroform. The organic layer is washed with water, brine (2.x.20 mL) and dried over anhydrous sodium sulfate. In the event that imine/ketone mixtures are obtained, it may be necessary to stir the triflic acid/ice/water mixture for few hours in order to ensure complete hydrolysis. The products are purified via column chromatography (silica gel; hexanes/ether).

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Rx-ID: 31460273 Find similar reactions

98%

With bismuth (III) nitrate pentahydrate; cellulose supported copper(0); oxygen in acetonitrile

T=60°C; 0.5 h;

Baruah, Diganta; Hussain, Farhaz L.; Suri, Mrinaly; Saikia, Ujwal Pratim; Sengupta, Pinaki; Dutta, Dipak Kumar; Konwar, Dilip

Catalysis Communications, 2016 , vol. 77, p. 9 - 12 Title/Abstract Full Text View citing articles Show Details

With copper(II) chloride monohydrate; potassium carbonate in N,N-dimethyl-formamide

T=60°C; 24 h;

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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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: 31460374 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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Rx-ID: 31571847 Find similar reactions

With Silica gel supported aluminium trichloride T=20°C; Friedel Crafts acylation; 1.1 h; neat (no solvent); regioselective reaction;

Boroujeni, Kaveh Parvanak

Chinese Chemical Letters, 2010 , vol. 21, # 12 p. 1395 - 1398 Title/Abstract Full Text View citing articles Show Details

With polystyrene supported aluminium triflate T=20°C; Friedel-Crafts acylation; 1.1 h; Neat (no solvent); regioselective reaction;

Boroujeni, Kaveh Parvanak

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3156 - 3158 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: oxygen; silver(I) acetate; palladium diacetate / anhydrous xylene / 6 h / 130 °C / Sealed tube 2: ethanol; sodium hydroxide / 3 h / 70 °C View Scheme

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Rx-ID: 32987727 Find similar reactions

Xie, Yongju; Yang, Yuzhu; Huang, Lehao; Zhang, Xunbin; Zhang, Yuhong

Organic Letters, 2012 , vol. 14, # 5 p. 1238 - 1241 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 32987735 Find similar reactions

Multi-step reaction with 2 steps 1: oxygen; silver(I) acetate; palladium diacetate / anhydrous xylene / 1 h / 130 °C / Sealed tube 2: ethanol; sodium hydroxide / 3 h / 70 °C View Scheme

Xie, Yongju; Yang, Yuzhu; Huang, Lehao; Zhang, Xunbin; Zhang, Yuhong

Organic Letters, 2012 , vol. 14, # 5 p. 1238 - 1241 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: oxygen; silver(I) acetate; palladium diacetate / anhydrous xylene / 24 h / 130 °C / Sealed tube 2: ethanol; sodium hydroxide / 3 h / 70 °C View Scheme

Xie, Yongju; Yang, Yuzhu; Huang, Lehao; Zhang, Xunbin; Zhang, Yuhong

Organic Letters, 2012 , vol. 14, # 5 p. 1238 - 1241 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 3 steps 1: oxygen; silver(I) acetate; palladium diacetate / anhydrous xylene / 1 h / 130 °C / Sealed tube 2: oxygen; silver(I) acetate; palladium diacetate / anhydrous

Xie, Yongju; Yang, Yuzhu; Huang, Lehao; Zhang, Xunbin; Zhang, Yuhong

Organic Letters, 2012 , vol. 14, # 5 p. 1238 - 1241 Title/Abstract Full Text View citing articles Show Details

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xylene / 6 h / 130 °C / Sealed tube 3: ethanol; sodium hydroxide / 3 h / 70 °C View Scheme

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Multi-step reaction with 3 steps 1: triethylamine; trichlorophosphate / dichloromethane / 2.5 h / 0 20 °C 2: oxygen; silver(I) acetate; palladium diacetate / anhydrous xylene / 6 h / 130 °C / Sealed tube 3: ethanol; sodium hydroxide / 3 h / 70 °C View Scheme

Rx-ID: 32987748 Find similar reactions

Xie, Yongju; Yang, Yuzhu; Huang, Lehao; Zhang, Xunbin; Zhang, Yuhong

Organic Letters, 2012 , vol. 14, # 5 p. 1238 - 1241 Title/Abstract Full Text View citing articles Show Details

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91%

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With ethanol; sodium hydroxide

T=70°C; 3 h;

Rx-ID: 32987749 Find similar reactions

Xie, Yongju; Yang, Yuzhu; Huang, Lehao; Zhang, Xunbin; Zhang, Yuhong

Organic Letters, 2012 , vol. 14, # 5 p. 1238 - 1241 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 1: triethylamine; trichlorophosphate / dichloromethane / 2.5 h / 0 20 °C 2: oxygen; silver(I) acetate; palladium diacetate / anhydrous

Rx-ID: 32987763 Find similar reactions

Xie, Yongju; Yang, Yuzhu; Huang, Lehao; Zhang, Xunbin; Zhang, Yuhong

Organic Letters, 2012 , vol. 14, # 5 p. 1238 - 1241 Title/Abstract Full Text View citing articles Show Details

xylene / 1 h / 130 °C / Sealed tube 3: ethanol; sodium hydroxide / 3 h / 70 °C View Scheme

Multi-step reaction with 3 steps 1: triethylamine; trichlorophosphate / dichloromethane / 2.5 h / 0 20 °C 2: oxygen; silver(I) acetate; palladium diacetate / anhydrous xylene / 24 h / 130 °C / Sealed tube 3: ethanol; sodium hydroxide / 3 h / 70 °C View Scheme

Xie, Yongju; Yang, Yuzhu; Huang, Lehao; Zhang, Xunbin; Zhang, Yuhong

Organic Letters, 2012 , vol. 14, # 5 p. 1238 - 1241 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 4 steps 1: triethylamine; trichlorophosphate / dichloromethane / 2.5 h / 0 20 °C 2: oxygen; silver(I) acetate; palladium diacetate / anhydrous xylene / 1 h / 130 °C / Sealed tube 3: oxygen; silver(I) acetate; palladium diacetate / anhydrous xylene / 6 h / 130 °C / Sealed tube 4: ethanol; sodium hydroxide / 3 h / 70 °C View Scheme

Xie, Yongju; Yang, Yuzhu; Huang, Lehao; Zhang, Xunbin; Zhang, Yuhong

Organic Letters, 2012 , vol. 14, # 5 p. 1238 - 1241 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 34777522 Find similar reactions

A: 11 %Chromat. B: 89 %Chromat.

With potassium carbonate

T=80°C; Suzuki Coupling; P=760.051 Torr; 12 h; Green chemistry;

Niu, Jian-Rui; Huo, Xing; Zhang, Feng-Wei; Wang, Hai-Bo; Zhao, Ping; Hu, Wu-Quan; Ma, Jiantai; Li, Rong

ChemCatChem, 2013 , vol. 5, # 1 p. 349 - 354 Title/Abstract Full Text View citing articles Show Details

A: 9 %Chromat. B: 85 %Chromat.

With potassium carbonate

T=80°C; Suzuki Coupling; P=760.051 Torr; 12 h; Green chemistry; Catalytic behavior; Hide Experimental Procedure

Niu, Jianrui; Xie, Miao; Zhu, Xiaohang; Long, Yu; Wang, Peng; Li, Rong; Ma, Jiantai

Journal of Molecular Catalysis A: Chemical, 2014 , vol. 392, p. 247 - 252 Title/Abstract Full Text View citing articles Show Details

3:2.2.4. Typical procedure for the carbonylative Suzuki couplingreaction

General procedure: A mixture of aryl iodide (0.5 mmol), arylboronic acid (0.6 mmol),K2CO3(1.5 mmol), and 2 molpercent palladium catalyst in anisole (5 mL)were stirred at 80C under 1 atm pressure of CO. An aliquot wastaken with a syringe and subjected to GC analysis and1H NMR (seethe supplementary material). Yields were calculated against theconsumption of the aryl iodides.

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Find similar Rx-ID: 35209932 Find similar reactions

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75%

Stage #1: in tetrahydrofuran

T=0 - 20°C; 13 h; Inert atmosphere; Stage #2: With hydrogenchloride in tetrahydrofuran; water

T=0 - 20°C; 12 h; Inert atmosphere;

Chen, Jia-Hua; Chen, Zi-Cong; Zhao, Hong; Zhang, Ting; Wang, Wei-Juan; Zou, Yong; Zhang, Xue-Jing; Yan, Ming

Organic and Biomolecular Chemistry, 2016 , vol. 14, # 17 p. 4071 - 4076 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: tetrahydrofuran / 20 h / 15 °C / |Inert atmosphere 2: hydrogenchloride; water / 0.5 h / 60 °C / |Inert atmosphere View Scheme

Mateos, Carlos; Rincon, Juan A.; Villanueva, Jose

Tetrahedron Letters, 2013 , vol. 54, # 18 p. 2226 - 2230 Title/Abstract Full Text View citing articles Show Details

in tetrahydrofuran

T=0 - 20°C; 1.08333 h; Inert atmosphere;

Li, Xiaoxun; Li, Hui; Song, Wangze; Tseng, Po-Sen; Liu, Lingyan; Guzei, Ilia A.; Tang, Weiping

Angewandte Chemie - International Edition, 2015 , vol. 54, # 44 p. 12905 - 12908 Title/Abstract Full Text View citing articles Show Details

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With hydrogenchloride; water

T=60°C; 0.5 h; Inert atmosphere;

Rx-ID: 35209943 Find similar reactions

Mateos, Carlos; Rincon, Juan A.; Villanueva, Jose

Tetrahedron Letters, 2013 , vol. 54, # 18 p. 2226 - 2230 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 36565893 Find similar reactions

82%

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Stage #1: 9-methyl-9H-fluorene-9-carbonyl chloride With N-ethylN,N-diisopropylamine; bis(dibenzylideneacetone)-palladium(0); tri tert-butylphosphoniumtetrafluoroborate

T=80°C; Stage #2: 2-iodophenylamine; phenylboronic acid With potassium carbonate; palladium dichloride

T=80°C;

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Ahlburg, Andreas; Lindhardt, Anders T.; Taaning, Rolf. H.; Modvig, Amalie E.; Skrydstrup, Troels

Journal of Organic Chemistry, 2013 , vol. 78, # 20 p. 10310 - 10318 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: palladium diacetate; trifluoroacetic acid; tert.-butylhydroperoxide / water / 24 h / 20 °C 2: hydrogenchloride / water / 3 h / 125 °C View Scheme

Rx-ID: 36978073 Find similar reactions

Szabo, Fruzsina; Simko, Daniel; Novak, Zoltan

RSC Advances, 2014 , vol. 4, # 8 p. 3883 - 3886 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 38015784 Find similar reactions

91%

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With [2,2']bipyridinyl; para-nitrobenzenesulfonic acid; palladium diacetate in tetrahydrofuran; water

T=80°C; 48 h; Inert atmosphereSchlenk technique; Reagent/catalystSolvent; 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.

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Rx-ID: 38867713 Find similar reactions

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80%

With silver carbonate in acetonitrile

T=60°C; 1 h;

Cheng, Kai; Zhao, Baoli; Qi, Chenze

RSC Advances, 2014 , vol. 4, # 89 p. 48698 - 48702 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 38901665 Find similar reactions

66%

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Ang, Wei Jie; Lo, Lee-Chiang; Lam, Yulin

Tetrahedron, 2014 , vol. 70, # 45 p. 8545 - 8558 Title/Abstract Full Text View citing articles Show Details

With C35H20F34NO3(1-)*Pd(2+)*Cl(1-); N,Ndiisopropylethylamine in water

T=140°C; 0.2 h; Microwave irradiation; Hide Experimental Procedure

11:Carbonylative Suzuki-Miyaura coupling of aryl halideand arylboronic acid: general procedure

General procedure: A mixture of the aryl halide (0.6 mmol), arylboronic acid (2.5 equiv), Mo(CO)6 (1.5 equiv), DIPEA (3.0 equiv), palladacycle 1 (1 mol percent Pd), and water (1.0 mL) was heated in a pressure tube at 140 °C under microwave irradiation. The reaction was monitored by TLC. When the reaction has completed, the reaction mixturewas cooled to room temperature, poured into EtOAc (20 mL) and washed successively with water (310 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated. The crude product was then purified by column chromatography to give pure 4.

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Rx-ID: 39166253 Find similar reactions

69%

With silver carbonate in acetonitrile

T=60°C; 1 h;

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Cheng, Kai; Zhao, Baoli; Qi, Chenze

RSC Advances, 2014 , vol. 4, # 89 p. 48698 - 48702 Title/Abstract Full Text View citing articles Show Details

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79%

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With cellulose supported Cu-nanoparticles in water

T=100°C; 0.133333 h; Microwave irradiationGreen chemistry;

Rx-ID: 39267108 Find similar reactions

Baruah, Diganta; Saikia, Ujwal Pratim; Pahari, Pallab; Dutta, Dipak Kumar; Konwar, Dilip

RSC Advances, 2014 , vol. 4, # 103 p. 59338 - 59343 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 39625063 Find similar reactions

83%

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With carbon monoxide; potassium carbonate in toluene

T=120°C; Suzuki Coupling; P=22502.3 Torr; 12 h; Autoclave;

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Jiao, Nianming; Li, Zelong; Wang, Yan; Liu, Jianhua; Xia, Chungu

RSC Advances, 2015 , vol. 5, # 34 p. 26913 - 26922 Title/Abstract Full Text View citing articles Show Details

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95%

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With palladium 10 on activated carbon; hydrogen; triethylamine in tetrahydrofuran

T=25°C; P=7500.75 Torr; 12 h; Autoclave;

Rx-ID: 42357735 Find similar reactions

Aidene, Mohand; Belkessam, Fatma; Soulé, Jean-François; Doucet, Henri

ChemCatChem, 2016 , vol. 8, # 8 p. 1583 - 1590 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 42357753 Find similar reactions

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Multi-step reaction with 2 steps 1: Pd(1,4-bis(diphenylphosphino)butane)Cl2; potassium acetate / N,N-dimethyl acetamide / 20 h / 150 °C / |Inert atmosphere 2: triethylamine; palladium 10 on activated carbon; hydrogen / tetrahydrofuran / 12 h / 25 °C / 7500.75 Torr / |Autoclave View Scheme

Aidene, Mohand; Belkessam, Fatma; Soulé, Jean-François; Doucet, Henri

ChemCatChem, 2016 , vol. 8, # 8 p. 1583 - 1590 Title/Abstract Full Text View citing articles Show Details

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60%

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With oxygen; caesium carbonate in dimethyl sulfoxide

T=140°C; 8 h; Mechanism; Reagent/catalystSolventTemperature; Hide Experimental Procedure

Rx-ID: 42672419 Find similar reactions

Yu, Jin; Moon, Hye Ran; Min, Beom Kyu; Kim, Jae Nyoung

Bulletin of the Korean Chemical Society, 2016 , vol. 37, # 6 p. 893 - 897 Title/Abstract Full Text View citing articles Show Details

2. Typical procedure for the synthesis of 2a

A solution of 2-phenylindole (1a, 97 mg, 0.5 mmol) and Cs2CO3 (326 mg, 1.0 mmol) in DMSO (1.5 mL) was heated to 140 °C for 8 h under O2 balloon atmosphere. After the usual aqueous extractive workup and column chromatographic purification process (hexanes/Et2O, 10:1), 2-aminobenzophenone (2a) was obtained as a yellow solid, 59 mg (60 percent). Other compounds were prepared similarly, and the spectroscopic data of compounds 2a-l, 4 and 5 are as follows. Compound 2a:1 60 percent; yellow solid, mp 108-110 °C (lit.1a 111-112 °C); 1H NMR (CDCl3, 300 MHz) δ 6.09 (s, 2H), 6.60 (t, J = 8.4 Hz, 1H), 6.74 (d, J = 8.4 Hz, 1H), 7.29 (t, J = 8.4 Hz, 1H), 7.42-7.49 (m, 3H), 7.50-7.56 (m, 1H), 7.61-7.67 (m, 2H); 13C NMR (CDCl3, 75 MHz) δ 115.48, 116.96, 118.12, 128.05, 129.09, 131.01, 134.21, 134.57, 140.06, 150.89, 199.07; ESIMS m/z 198 [M++H].

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Synthesize Find similar Rx-ID: 42799683 Find similar reactions

Multi-step reaction with 2 steps 1.1: neat (no solvent) / 0.08 h / 100 °C 2.1: copper(II) bis(trifluoromethanesulfonate) / neat (no solvent) / 2 h / 150 °C 2.2: 1 h / 150 °C View Scheme

Tran, Phuong Hoang; Phung, Huy Quang; Hansen, Poul Erik; Tran, Hai Ngoc; Le, Thach Ngoc

Synthetic Communications, 2016 , vol. 46, # 10 p. 893 - 901 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 42799689 Find similar reactions

Stage #1: With copper(II) bis(trifluoromethanesulfonate) in neat (no solvent) T=150°C; Friedel-Crafts Acylation; 2 h; Stage #2: With sulfuric acid; water; acetic acid

T=150°C; 1 h; regioselective reaction;

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Tran, Phuong Hoang; Phung, Huy Quang; Hansen, Poul Erik; Tran, Hai Ngoc; Le, Thach Ngoc

Synthetic Communications, 2016 , vol. 46, # 10 p. 893 - 901 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: tetrahydrofuran / 1 h / -78 °C 2: palladium on activated charcoal; acetic acid; hydrogen / methanol / 5 h / 20 °C / 760.05 Torr View Scheme

Rx-ID: 42947360 Find similar reactions

Chen, Jia-Hua; Chen, Zi-Cong; Zhao, Hong; Zhang, Ting; Wang, Wei-Juan; Zou, Yong; Zhang, Xue-Jing; Yan, Ming

Organic and Biomolecular Chemistry, 2016 , vol. 14, # 17 p. 4071 - 4076 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 43224228 Find similar reactions

63%

With palladium(II) trifluoroacetate; 1,2-bis(diphenylphosphino)ethane in N,N-dimethyl acetamide

T=80°C; Suzuki-Miyaura Coupling; P=760.051 Torr; 6 h;

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Hao, Cheng Yi; Wang, Dan; Li, Ya Wei; Dong, Lin Lin; Jin, Ying; Zhang, Xiu Rong; Zhu, He Yun; Chang, Sheng

RSC Advances, 2016 , vol. 6, # 89 p. 86502 - 86509 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 43224229 Find similar reactions

71%

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With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)phosphane; palladium(II) trifluoroacetate in tert-butyl methyl ether

T=80°C; Suzuki-Miyaura Coupling; P=760.051 Torr; 6 h;

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Hao, Cheng Yi; Wang, Dan; Li, Ya Wei; Dong, Lin Lin; Jin, Ying; Zhang, Xiu Rong; Zhu, He Yun; Chang, Sheng

RSC Advances, 2016 , vol. 6, # 89 p. 86502 - 86509 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: copper(l) chloride / dichloromethane / 24 h / 23 °C / |Inert atmosphere; |Sealed tube 2: caesium carbonate / N,N-dimethyl-formamide / 12 h / 0 - 23 °C / |Inert atmosphere View Scheme

Rx-ID: 44733716 Find similar reactions

Klare, Hendrik F. T.; Goldberg, Alexander F. G.; Duquette, Douglas C.; Stoltz, Brian M.

Organic Letters, 2017 , vol. 19, # 5 p. 988 - 991 Title/Abstract Full Text Show Details