Query Query
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Date
24 reactions in Reaxys
2018-05-03 21h:04m:25s (UTC)
H 2N O
1. Query N
O
O
Search as: Product, As drawn, No mixtures ))
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O O
N H 2N
N O
O
O
N O N
O
NH O
Rx-ID: 41706076 View in Reaxys 1/24 Yield 28 %, 30 %
Conditions & References With potassium tert-butylate in N,N-dimethyl-formamide, Time= 5h, T= 20 °C , Inert atmosphere Wei, Wen-Tao; Cheng, Ya-Juan; Hu, Yu; Chen, Yan-Yan; Zhang, Xue-Jing; Zou, Yong; Yan, Ming; Advanced Synthesis and Catalysis; vol. 357; nb. 16-17; (2015); p. 3474 - 3478 View in Reaxys H 2N
H 2N
O
O S–
O N
Na +
O
N
N
O
O O
Rx-ID: 38015791 View in Reaxys 2/24 Yield 96 %
Conditions & References 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. With p-nitrobenzenesulfonic acid, palladium diacetate in tetrahydrofuran, water, Time= 48h, T= 80 °C , Inert atmosphere, Schlenk technique Chen, Jiuxi; Li, Jianjun; Su, Weike; Molecules; vol. 19; nb. 5; (2014); p. 6439 - 6449 View in Reaxys H 2N
H 2N
O
HO B
O N
HO
N
N
O
O O
Rx-ID: 39047995 View in Reaxys 3/24 Yield 97 %
Conditions & References With 5,5'-dimethyl-2,2'-bipyridine, methanesulfonic acid, palladium(II) trifluoroacetate, water in 2-methyltetrahydrofuran, Time= 36h, T= 80 °C , Schlenk technique Chen, Jiuxi; Ye, Leping; Su, Weike; Organic and Biomolecular Chemistry; vol. 12; nb. 41; (2014); p. 8204 - 8211 View in Reaxys
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O H 2N
N
N
N O
N
O
O
N O
O
Rx-ID: 29592792 View in Reaxys 4/24 Yield
Conditions & References Stage 1: With 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride, tert-butyl alcohol in tetrahydrofuran, Time= 0.0833333h, T= 20 °C , Inert atmosphere Stage 2: With sodium t-butanolate in tetrahydrofuran, Time= 12h, T= 20 °C , Inert atmosphere, chemoselective reaction
60 %
Burnley, James; Carbone, Giorgio; Moses, John E.; Synlett; vol. 24; nb. 5; (2013); p. 652 - 656; Art.No: ST-2013-D0038-L View in Reaxys Ca. 10 %Spectr.
With iron(II) bromide in dichloromethane, Time= 16h, T= 40 °C , Inert atmosphere, Molecular sieve Stokes, Benjamin J.; Vogel, Carl V.; Urnezis, Linda K.; Pan, Minjie; Driver, Tom G.; Organic Letters; vol. 12; nb. 12; (2010); p. 2884 - 2887 View in Reaxys H 2N O
O
O N
NH 2
O
Cl
N
O
O
Rx-ID: 36590788 View in Reaxys 5/24 Yield
Conditions & References With zinc(II) chloride Singh, Rajesh K.; Prasad; Bhardwaj; Medicinal Chemistry Research; vol. 22; nb. 12; (2013); p. 5901 - 5911 View in Reaxys I
H 2N
O
O
N
O
O
N
O
O
Rx-ID: 30741270 View in Reaxys 6/24 Yield 50 %
Conditions & References Stage 1: With copper(l) iodide, D-glucosamine hydrochloride, potassium carbonate in water, acetone, Time= 0.166667h, T= 90 °C Stage 2: With ammonia in water, acetone, Time= 30h, T= 90 °C Thakur, Krishna Gopal; Ganapathy, Dhandapani; Sekar, Govindasamy; Chemical Communications; vol. 47; nb. 17; (2011); p. 5076 - 5078 View in Reaxys
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H 2N
N O
O O N O
N
O
O
Rx-ID: 2568931 View in Reaxys 7/24 Yield 99 %
Conditions & References With trimethylsilyl iodide, water in acetonitrile, Time= 0.5h, T= 20 °C Boruah, Monalisa; Konwar, Dilip; Journal of Chemical Research - Part S; nb. 12; (2002); p. 601 - 603 View in Reaxys
87 %
With Saccharomyces cerevisiae bakers' yeast in methanol, Time= 6h, T= 20 °C , pH= 7, aq. phosphate buffer, Microbiological reaction, shaking Lekhok, Kushal C.; Prajapati, Dipak; Boruah, Ramesh C.; Mazumder, Sharbani; Borah, Tarun C.; Monatshefte fur Chemie; vol. 140; nb. 10; (2009); p. 1183 - 1187 View in Reaxys With trimethylsilyl iodide, water, 1.) chloroform, room temperature, 4 h, 2.) 1 h, Yield given. Multistep reaction Konwar, D.; Boruah, R. C.; Sandhu, J. S.; Baruah, J. N.; Synthetic Communications; vol. 14; nb. 11; (1984); p. 1053 - 1058 View in Reaxys
H 2N
N O
O
N
N O N
NH 2
O
O
Rx-ID: 4936277 View in Reaxys 8/24 Yield 94 %
Conditions & References With triethylene diamine nickel thiosulfate, water in chloroform, Time= 0.0833333h, T= 20 °C , Hydrolysis Kamal; Arifuddin; Rao; Synlett; nb. 10; (2000); p. 1482 - 1484 View in Reaxys
90 %
With potassium carbonate, dimethyl sulfate in acetonitrile, Heating Kamal, Ahmed; Arifuddin; Rao, N. Venugopal; Synthetic Communications; vol. 28; nb. 21; (1998); p. 3927 - 3931 View in Reaxys H 2N
O
O
O
O O
N
N O
O
N
H 2N
O
O
Rx-ID: 4932466 View in Reaxys 9/24 Yield 21 %, 28 %
Conditions & References With potassium tert-butylate, N,N-tetramethylene-thiocarbamoyl-sulphenamide in N,N-dimethyl-formamide, Time= 0.333333h, T= 20 °C Makosza, Mieczyslaw; Bialecki, Maciej; Journal of Organic Chemistry; vol. 63; nb. 15; (1998); p. 4878 - 4888 View in Reaxys
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O
H N
H 2N O
O N
N O N
O
O
Rx-ID: 5017156 View in Reaxys 10/24 Yield
Conditions & References With hydrogenchloride Cox, Philip J.; Anisuzzaman, Abu T. M.D.; Howard Pryce-Jones; Skellern, Graham G.; Florence, Alastair J.; Shankland, Norman; Acta Crystallographica Section C: Crystal Structure Communications; vol. 54; nb. 6; (1998); p. 856 - 859 View in Reaxys H 2N
O HN
O
N O N
O
O
O
Rx-ID: 2109375 View in Reaxys 11/24 Yield
Conditions & References
90 %
in water, Irradiation, sodium dodecyl sulfate micelles Singh, A. K.; Raghuraman, T. S.; Synthetic Communications; vol. 16; nb. 4; (1986); p. 485 - 490 View in Reaxys
O
H N
O H 2N
N
O
O
O N
HO
N
NH 2
O
O
O N
O
NH O
H 2N
O
Rx-ID: 3778399 View in Reaxys 12/24 Yield
Conditions & References With hydrogenchloride, sodium dodecyl sulfate (sds), water in 1,4-dioxane, Time= 30h, T= 68 °C , N-alkylated nitrazepam derivatives; var. conc. of reagents, Mechanism, Product distribution Broxton; Morrison; Australian Journal of Chemistry; vol. 38; nb. 7; (1985); p. 1037 - 1043 View in Reaxys O
O H 2N
HN O O
OH
N
O
O
N O
O
Rx-ID: 1971656 View in Reaxys 13/24 Yield
Conditions & References With hydrogenchloride, T= 68.5 °C , var. concentration of HCl; also in the presence of sodium dodecyl sulfate, Rate constant
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Broxton; Ryan; Morrison; Australian Journal of Chemistry; vol. 37; nb. 9; (1984); p. 1895 - 1902 View in Reaxys O
H 2N N
O
O
O
N
O
NH
O H 2N
O
Rx-ID: 3824668 View in Reaxys 14/24 Yield
Conditions & References With hydrogenchloride, var. concentration of HCl, Rate constant Broxton; Ryan; Morrison; Australian Journal of Chemistry; vol. 37; nb. 9; (1984); p. 1895 - 1902 View in Reaxys H 2N O
N
O
O
Rx-ID: 6053035 View in Reaxys 15/24 Yield
Conditions & References Fryer et al.; Journal of Organic Chemistry; vol. 32; (1967); p. 3798,3802 View in Reaxys Vichljaev et al.; Fiziologicheski Aktivnye Veshchestva (1966-1992); vol. 3; (1971); p. 265,266-279; ; vol. 77; nb. 88459e; Chem. Zentralbl.; Ref.Zh.Khim. 1971, 17, 351 View in Reaxys Lafargue; Pont; Meunier; Annales pharmaceutiques francaises; vol. 28; nb. 5; (1970); p. 343 - 354 View in Reaxys Nelson; Chemistry and Industry (London, United Kingdom); (1965); p. 653 View in Reaxys Pribilla; Arzneimittel Forschung; vol. 15; (1965); p. 1148,1149 View in Reaxys Beyer; Sadée; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 302; nb. 2; (1969); p. 152 - 157 View in Reaxys Patent; Hoffmann-LaRoche; BE648149; (1964); ; vol. 63; nb. 14889h; (1965) View in Reaxys Patent; Roehnert et al.; DD74798; (1970); ; vol. 74; nb. 87622d; (1971) View in Reaxys Patent; Delmar Chemicals; DE1811785; (1967); ; vol. 71; nb. 123960m; (1969) View in Reaxys Makasza; Jawdosiuk; Ludwikow; Przemysl Chemiczny; vol. 56; nb. 12; (1977); p. 636 - 637 View in Reaxys Patent; Hoffmann - La Roche; NL6405644; (1964); ; vol. 62; nb. 16137d; (1965) View in Reaxys Patent; Delmar Chemicals; DE1811785; (1969); ; vol. 71; nb. 123960 View in Reaxys
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H 2N O 14C
N
O
O
Rx-ID: 7832467 View in Reaxys 16/24 Yield
Conditions & References aus 2-Chlor-5-nitro-benzophenon-(carbonyl-14C), NH3 Yoshitake et al.; Journal of Labelled Compounds; vol. 8; (1972); p. 615,619 View in Reaxys O
O H 2N
HN O
N
O
O
N O
O
Rx-ID: 262695 View in Reaxys 17/24 Yield
Conditions & References With hydrogenchloride Atkinson et al.; Journal of the Chemical Society; (1954); p. 165,170 View in Reaxys
H 2N
NH O
O N O N
O
O
Rx-ID: 22221532 View in Reaxys 18/24 Yield
Conditions & References Reaction Steps: 2 1: acetic acid; aqueous CrO3 2: aq.-ethanolic HCl With chromium(VI) oxide, hydrogenchloride, acetic acid Atkinson et al.; Journal of the Chemical Society; (1954); p. 165,170 View in Reaxys H 2N O
O
N N
NH N
O
O O
Rx-ID: 22235863 View in Reaxys 19/24 Yield
Conditions & References Reaction Steps: 3 1: concentrated aqueous hydrochloric acid; acetic acid 2: acetic acid; aqueous CrO3 3: aq.-ethanolic HCl
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With chromium(VI) oxide, hydrogenchloride, acetic acid Atkinson et al.; Journal of the Chemical Society; (1954); p. 165,170 View in Reaxys O N O
H 2N
O O
N H N
O
O
O
Rx-ID: 402236 View in Reaxys 20/24 Yield
Conditions & References With hydrogenchloride, acetic acid Schofield; Theobald; Journal of the Chemical Society; (1950); p. 1505,1508 View in Reaxys Cl
H 2N
O
O
N
O
N
O
O
O
Rx-ID: 325511 View in Reaxys 21/24 Yield
Conditions & References With ammonia, T= 160 °C , im geschlossenen Rohr Ullmann; Mallet; Chemische Berichte; vol. 31; (1898); p. 1695 View in Reaxys Cl
H 2N
O
O
H
H N H
N
O
N
O
O
O
Rx-ID: 7448359 View in Reaxys 22/24 Yield
Conditions & References T= 160 °C Ullmann; Mallet; Chemische Berichte; vol. 31; (1898); p. 1695 View in Reaxys H 2N
Cl
O
O
O N N
Cl
O
O O
Rx-ID: 22043106 View in Reaxys 23/24 Yield
Conditions & References Reaction Steps: 2
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1: AlCl3 2: alcoholic ammonia / 160 °C / im geschlossenen Rohr With aluminium trichloride, ammonia Ullmann; Mallet; Chemische Berichte; vol. 31; (1898); p. 1695 View in Reaxys H 2N O
N
O
O
Rx-ID: 22072162 View in Reaxys 24/24 Yield
Conditions & References Reaction Steps: 2 1: AlCl3 2: alcoholic ammonia / 160 °C / im geschlossenen Rohr With aluminium trichloride, ammonia Ullmann; Mallet; Chemische Berichte; vol. 31; (1898); p. 1695 View in Reaxys
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