Query Query
Results
Date
36 reactions in Reaxys
2017-11-06 12h:42m:30s (EST)
36 reactions in Reaxys
2017-11-06 12h:43m:26s (EST)
O
1. Query
O O O
O
Search as: As drawn 2. Query
(1. Query) AND itemno in (1)
Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
1/12
2017-11-06 12:48:25
O
O
O
O O
O O
O
O O
O
Rx-ID: 646778 View in Reaxys 1/36 Yield 74 %
Conditions & References Stage 1: With sodium ethanolate in benzene, T= 0 °C , Inert atmosphere Stage 2: in benzene, Time= 14.5h, T= 0 - 20 °C , Inert atmosphere Riahi, Abdolmajid; Shkoor, Mohanad; Fatunsin, Olumide; Khera, Rasheed Ahmad; Fischer, Christine; Langer, Peter; Organic and Biomolecular Chemistry; vol. 7; nb. 20; (2009); p. 4248 - 4251 View in Reaxys With diethyl ether, sodium ethanolate, Behandeln in Wasser mit verduennter Schwefelsaeure in Gegenwart von Aether Wislicenus; Justus Liebigs Annalen der Chemie; vol. 246; (1888); p. 324 View in Reaxys Piutti; Gazzetta Chimica Italiana; vol. 17; (1887); p. 520; Gazzetta Chimica Italiana; vol. 20; (1890); p. 169,170 View in Reaxys Patent; Hoechster Farbw.; DE43847; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 1; p. 218,597 View in Reaxys With diethyl ether, sodium, Behandeln in Wasser mit verduennter Schwefelsaeure in Gegenwart von Aether Wislicenus; Justus Liebigs Annalen der Chemie; vol. 246; (1888); p. 324 View in Reaxys Piutti; Gazzetta Chimica Italiana; vol. 17; (1887); p. 520; Gazzetta Chimica Italiana; vol. 20; (1890); p. 169,170 View in Reaxys Patent; Hoechster Farbw.; DE43847; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 1; p. 218,597 View in Reaxys With sodium Graf; Liu; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 300; nb. 4; (1967); p. 348 - 353 View in Reaxys With C2H6O*Na(1+) in diethyl ether, Heating, overnight Campaigne, E.; McLaughlin, Astley R.; Journal of Heterocyclic Chemistry; vol. 20; (1983); p. 623 - 628 View in Reaxys With sodium ethanolate in diethyl ether Nepveu, Francoise; Gaultier, Nicolas; Korber, Nikolaus; Jaud, Joel; Castan, Paule; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 24; (1995); p. 4005 - 4014 View in Reaxys With sodium in ethanol, Time= 3h, T= 0 - 40 °C , Inert atmosphere Hu, Bing C.; Zhou, Wei Y.; Liu, Zu L.; Cai, Chao J.; Xu, Shi C.; Journal of Porphyrins and Phthalocyanines; vol. 14; nb. 1; (2010); p. 89 - 100 View in Reaxys With sodium hexamethyldisilazane in tetrahydrofuran, T= -78 - 0 °C Barawkar, Dinesh A.; Bandyopadhyay, Anish; Deshpande, Anil; Koul, Summon; Kandalkar, Sachin; Patil, Pradeep; Khose, Goraksha; Vyas, Samir; Mone, Mahesh; Bhosale, Shubhangi; Singh, Umesh; De, Siddhartha; Meru, Ashwin; Gundu, Jayasagar; Chugh, Anita; Palle, Venkata P.; Mookhtiar, Kasim A.; Vacca, Joseph P.; Chakravarty, Prasun K.; Nargund, Ravi P.; Wright, Samuel D.; Roy, Sophie; Graziano, Michael P.; Cully, Doris; Cai, Tian-Quan; Singh, Sheo B.; Bioorganic and Medicinal Chemistry Letters; vol. 22; nb. 13; (2012); p. 4341 - 4347 View in Reaxys A : Step A Diethyl 2-oxosuccinate (11a)
Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
2/12
2017-11-06 12:48:25
Step A Diethyl 2-oxosuccinate (11a); To a solution of sodium hydride (14 g, 60percentw/w, 580 mmol) in THF at 65°C; a solution of diethyl oxalate (43 g, 295 mmol) in ethyl acetate (20 g, 295 mmol) and was added drop wise using an addition funnel for about 2h until the reaction mixture turned pale yellow. The reaction mixture was slowly brought to room temperature and stirred for additional lh. The reaction mixture was cooled to 0°C and acidified with concentrated H2SO4 until pH 3. The reaction mixture was filtered through a celite bed and concentrated under reduced pressure to get 11a as a pale yellow liquid. With sodium hydride in tetrahydrofuran, ethyl acetate, Time= 3h, T= 15 - 65 °C Patent; MERCK SHARP and DOHME CORP.; BARR, Kenneth, Jay; SCOTT, Mark, E.; THOMPSON, Christopher, F.; ANTHONY, Neville; CAMMARANO, Carolyn, Michelle; BAKSHI, Raman, Kumar; MOHANTY, Subhendu, Kumar; KORAPALA, Chandra, Sekhar; LATTHE, Prashant, R.; KAMBAM, Vyjayanthi, N.; SARKAR, Sujit, Kumar; THATAI, Jayanth, Thiruvellore; WO2015/50798; (2015); (A1) English View in Reaxys 38 g
1.1 : Synthesis of diethyl oxaloacetate 30 g of ethyl acetate was added to 400 ml of anhydrous tetrahydrofuran,46 g of sodium ethoxide was added, heated under reflux for 1 hour,Cooled to room temperature, 50 g of diethyl oxalate was added, stirred for 4 hours under reflux,Concentrated and then ethyl acetate and water were added, separated, dried and concentrated, and the residue was separated on column to give 38 g of diethyl oxaloacetate. Stage 1: With sodium ethanolate in tetrahydrofuran, Time= 1h, Reflux Stage 2: in tetrahydrofuran, Time= 4h, Reflux Patent; (5 pag.); CN106854181; (2017); (A) Chinese View in Reaxys
38 g
1.1 : (1) Synthesis of diethyl oxaloacetate 30 g of ethyl acetate was added to 400 ml of anhydrous tetrahydrofuran, and 46 g of sodium ethoxide was added, followed by heating under reflux for 1 hour,But further to 50 g of diethyl oxalate, stirred for 4 hours, concentrated and then added with ethyl acetate and water, separated, dried and concentrated. The residue was separated on column to give 38 g of diethyl oxaloacetate. Stage 1: With sodium ethanolate in tetrahydrofuran, Time= 1h, Reflux Stage 2: in tetrahydrofuran, Time= 4h Patent; Hunan Huateng Pharmaceutical Co., Ltd.; Deng Zeping; Li Shuyun; (5 pag.); CN106749039; (2017); (A) Chinese View in Reaxys
O
O
O
O
O
O
O
O
O O
O
Rx-ID: 43839153 View in Reaxys 2/36 Yield
Conditions & References With sodium hydride in toluene, Reflux Son, Jeong-Yu; Kim, Jonghye; Han, Sang Hoon; Kim, Sung Hong; Lee, Phil Ho; Organic Letters; vol. 18; nb. 20; (2016); p. 5408 - 5411 View in Reaxys O
O O
O
O
O O
O
O
Rx-ID: 38411818 View in Reaxys 3/36 Yield 42 %
Conditions & References With water, platinum (II) chloride in methanol, T= 60 °C Chen, Qian; Zhang, Changyuan; Wen, Chunxiao; Fang, Jin; Du, Zhiyun; Wu, Dongling; Catalysis Communications; vol. 56; (2014); p. 101 - 105
Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
3/12
2017-11-06 12:48:25
View in Reaxys O
O O
Z O
O
O
Na +
O–
O O
O
Rx-ID: 25685445 View in Reaxys 4/36 Yield
Conditions & References Preparation of Intermediate ethyl 5-(2-chlorophenyl)-1-(4-chlorophenyl)-3-hvdroxy-2-oxo-2,5- dihydro- 1 H-pyrrole-4carboxylate (l-3a):l-3a A solution of 20.0 g (142 mmol) of 2- chlorobenzaidehyde and 18.2 g (142 mmol) of 4- chloroaniline in 200 ml of absolute ethanol was stirred at room temperature for 16 hours. The solvent was evaporated, the residue was triturated with i-PrOH and collected by filtration to give 33.7 g (95percent) of imine.A solution of 31.1 g (148 mmol) of diethyloxalacetate sodium salt in water was layered with ether and acidified with concentrated sulfuric acid. After agitation, the layers were separated and the aqueous phase extracted twice more with ether. The combined organic layers were dried (magnesium sulfate) and filtered. The imine prepared above was added to the ether solution of diethyloxalacetate and the mixture stirred at room temperature for 4 days. The solvent was evaporated, the residue was triturated with ether and collected by filtration to give 41.2 g (78percent) of the title compound (K3a). 1 H NMR (CDCI ): δ 1.16 (t, J = 7.1 Hz, 3H), 4.17 (m,2H), 6.39 (s, 1 H), 6.92 (dd, J = 7.6, 1.8 Hz, 1 H), 7.11 -7.27 (m, 3 4H), 7.35 (dd, J = 7.6, 1.4 Hz, 1 H), 7.50 (m, 2H). With sulfuric acid in diethyl ether, water Patent; PHARMACIA and UPJOHN COMPANY LLC; WO2007/20502; (2007); (A2) English View in Reaxys
H 2N
O N
O
O
H 2N H
O
O
H O
O
O
O
Rx-ID: 3144949 View in Reaxys 5/36 Yield
Conditions & References With sulfuric acid in water, Time= 2h, Ambient temperature, Yield given Ikota; Achiwa; Yamada; Chemical and Pharmaceutical Bulletin; vol. 31; nb. 3; (1983); p. 887 - 894 View in Reaxys
O O O
H 2N
N
O
H O
H
O
O O
H 2N
O
Rx-ID: 3145992 View in Reaxys 6/36 Yield
Conditions & References With sulfuric acid in water, Time= 2h, Ambient temperature, Yield given Ikota; Achiwa; Yamada; Chemical and Pharmaceutical Bulletin; vol. 31; nb. 3; (1983); p. 887 - 894 View in Reaxys
H O
O
NH 2 O
O O
O
bromoethoxycarbonylmethylene-4-nitro-phenylhydrazine
O O
O
Rx-ID: 20089486 View in Reaxys 7/36
Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
4/12
2017-11-06 12:48:25
Yield
Conditions & References Reaction Steps: 5 1: benzene / 72 h / Heating 2: H2 / 5percent palladium on charcoal / ethanol / 16 h / Ambient temperature 3: tert-butyl hypochlorite / diethyl ether / 0.5 h / 0 °C 4: sodium ethoxide / ethanol / 1 h / 40 °C 5: 5percent sulfuric acid / H2O / 2 h / Ambient temperature With tert-butylhypochlorite, sulfuric acid, hydrogen, sodium ethanolate, palladium on activated charcoal in diethyl ether, ethanol, water, benzene Ikota; Achiwa; Yamada; Chemical and Pharmaceutical Bulletin; vol. 31; nb. 3; (1983); p. 887 - 894 View in Reaxys Reaction Steps: 5 1: benzene / 48 h / Heating 2: H2 / 5percent palladium on charcoal / ethanol / 16 h / Ambient temperature 3: tert-butyl hypochlorite / diethyl ether / 0.5 h / 0 °C 4: sodium ethoxide / ethanol / 1 h / 40 °C 5: 5percent sulfuric acid / H2O / 2 h / Ambient temperature With tert-butylhypochlorite, sulfuric acid, hydrogen, sodium ethanolate, palladium on activated charcoal in diethyl ether, ethanol, water, benzene Ikota; Achiwa; Yamada; Chemical and Pharmaceutical Bulletin; vol. 31; nb. 3; (1983); p. 887 - 894 View in Reaxys
O
O O O
N O
Cl
bromoethoxycarbonylmethylene-4-nitro-phenylhydrazine
O O
O
O
Rx-ID: 20107672 View in Reaxys 8/36 Yield
Conditions & References Reaction Steps: 2 1: sodium ethoxide / ethanol / 1 h / 40 °C 2: 5percent sulfuric acid / H2O / 2 h / Ambient temperature With sulfuric acid, sodium ethanolate in ethanol, water Ikota; Achiwa; Yamada; Chemical and Pharmaceutical Bulletin; vol. 31; nb. 3; (1983); p. 887 - 894 View in Reaxys
O O O
O
O
N
O
bromoethoxycarbonylmethylene-4-nitro-phenylhydrazine
O
O O
Rx-ID: 20107791 View in Reaxys 9/36 Yield
Conditions & References Reaction Steps: 4 1: H2 / 5percent palladium on charcoal / ethanol / 16 h / Ambient temperature 2: tert-butyl hypochlorite / diethyl ether / 0.5 h / 0 °C 3: sodium ethoxide / ethanol / 1 h / 40 °C 4: 5percent sulfuric acid / H2O / 2 h / Ambient temperature With tert-butylhypochlorite, sulfuric acid, hydrogen, sodium ethanolate, palladium on activated charcoal in diethyl ether, ethanol, water Ikota; Achiwa; Yamada; Chemical and Pharmaceutical Bulletin; vol. 31; nb. 3; (1983); p. 887 - 894
Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
5/12
2017-11-06 12:48:25
View in Reaxys
O
O
O
O
O
bromoethoxycarbonylmethylene-4-nitro-phenylhydrazine
O
N
O
O
O
Rx-ID: 20107898 View in Reaxys 10/36 Yield
Conditions & References Reaction Steps: 4 1: H2 / 5percent palladium on charcoal / ethanol / 16 h / Ambient temperature 2: tert-butyl hypochlorite / diethyl ether / 0.5 h / 0 °C 3: sodium ethoxide / ethanol / 1 h / 40 °C 4: 5percent sulfuric acid / H2O / 2 h / Ambient temperature With tert-butylhypochlorite, sulfuric acid, hydrogen, sodium ethanolate, palladium on activated charcoal in diethyl ether, ethanol, water Ikota; Achiwa; Yamada; Chemical and Pharmaceutical Bulletin; vol. 31; nb. 3; (1983); p. 887 - 894 View in Reaxys
O O
O
bromoethoxycarbonylmethylene-4-nitro-phenylhydrazine
O
NH
O
O
O
O O
Rx-ID: 20108242 View in Reaxys 11/36 Yield
Conditions & References Reaction Steps: 3 1: tert-butyl hypochlorite / diethyl ether / 0.5 h / 0 °C 2: sodium ethoxide / ethanol / 1 h / 40 °C 3: 5percent sulfuric acid / H2O / 2 h / Ambient temperature With tert-butylhypochlorite, sulfuric acid, sodium ethanolate in diethyl ether, ethanol, water Ikota; Achiwa; Yamada; Chemical and Pharmaceutical Bulletin; vol. 31; nb. 3; (1983); p. 887 - 894 View in Reaxys
O
Cl N
O
O O
O
bromoethoxycarbonylmethylene-4-nitro-phenylhydrazine
O O
O
O
Rx-ID: 20108301 View in Reaxys 12/36 Yield
Conditions & References Reaction Steps: 2 1: sodium ethoxide / ethanol / 1 h / 40 °C 2: 5percent sulfuric acid / H2O / 2 h / Ambient temperature With sulfuric acid, sodium ethanolate in ethanol, water Ikota; Achiwa; Yamada; Chemical and Pharmaceutical Bulletin; vol. 31; nb. 3; (1983); p. 887 - 894 View in Reaxys
Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
6/12
2017-11-06 12:48:25
O
O
O
O
O
bromoethoxycarbonylmethylene-4-nitro-phenylhydrazine
O
NH
O
O
O
Rx-ID: 20108564 View in Reaxys 13/36 Yield
Conditions & References Reaction Steps: 3 1: tert-butyl hypochlorite / diethyl ether / 0.5 h / 0 °C 2: sodium ethoxide / ethanol / 1 h / 40 °C 3: 5percent sulfuric acid / H2O / 2 h / Ambient temperature With tert-butylhypochlorite, sulfuric acid, sodium ethanolate in diethyl ether, ethanol, water Ikota; Achiwa; Yamada; Chemical and Pharmaceutical Bulletin; vol. 31; nb. 3; (1983); p. 887 - 894 View in Reaxys O O
O O
O
Rx-ID: 6190299 View in Reaxys 14/36 Yield
Conditions & References Shinohara et al.; Nippon Kagaku Zasshi; vol. 83; (1962); p. 618 View in Reaxys Carabateas; Williams; Journal of Heterocyclic Chemistry; vol. 13; (1976); p. 927 View in Reaxys Gault et al.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 254; (1962); p. 2993 View in Reaxys Tschchikwadse; Magidson; Meditsinskaya Promyshlennost SSSR; vol. 14; nb. 10; (1960); p. 24,25, 26; ; nb. 6487; (1961) View in Reaxys Wiley; Kim; Journal of Organic Chemistry; vol. 38; (1973); p. 3582,3585 View in Reaxys Lewis; Seifert; Organic Preparations and Procedures International; vol. 3; (1971); p. 243 View in Reaxys Sucrow; Grosz; Synthetic Communications; vol. 9; (1979); p. 603 View in Reaxys Hay; Australian Journal of Chemistry; vol. 17; (1964); p. 759,760, 763 View in Reaxys Bigg; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 12; (1976); p. 571,573,574 View in Reaxys Iha; Bahore; Journal of the Indian Chemical Society; vol. 48; (1971); p. 645,646-648 View in Reaxys Hojo; Mukaiyama; Chemistry Letters; (1978); p. 369,370 View in Reaxys Angulo et al.; Anales de la Real Sociedad Espanola de Fisica y Quimica, Serie B: Quimica; vol. 56; (1960); p. 761 View in Reaxys O
O Cl
O Cl
O– Na +
O
O
O O
O
Rx-ID: 1148369 View in Reaxys 15/36 Yield
Conditions & References in ethanol Levas,M.; Levas,E.; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 264; (1967); p. 907 - 910
Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
7/12
2017-11-06 12:48:25
View in Reaxys O
OH O
E
O O
air
O
aqueous solutions of pH > 11
O HO
O
O
O O
O
OH
O
O
Rx-ID: 7066318 View in Reaxys 16/36 Yield
Conditions & References Elkik; ; vol. 8; (1957); p. 176,188 View in Reaxys O
O O
O
O
Cl O
O O
O
Rx-ID: 656133 View in Reaxys 17/36 Yield
Conditions & References With sulfur dioxide, T= 65 °C , Behandeln des Reaktionsprodukts mit Aethanol. Smrt et al.; Collection of Czechoslovak Chemical Communications; vol. 20; (1955); p. 285,289 View in Reaxys O
O O
O
liquid sulfur dioxide
Cl O
O
O O
O
Rx-ID: 6190301 View in Reaxys 18/36 Yield
Conditions & References anschliessenden Behandeln mit Aethanol Smrt et al.; Collection of Czechoslovak Chemical Communications; vol. 20; (1955); p. 285,289 View in Reaxys Cl
O
O
Cl
O
liquid sulfur dioxide O
O
O
O
O
O O
O
O O
O
Rx-ID: 6684842 View in Reaxys 19/36 Yield
Conditions & References Behandeln des Reaktionsprodukts mit Aethanol Smrt et al.; Collection of Czechoslovak Chemical Communications; vol. 20; (1955); p. 285,289 View in Reaxys
Cl
O
O
O
O O
Cl
O O
O
Rx-ID: 59920 View in Reaxys 20/36 Yield
Conditions & References With chloroform, T= 65 °C , Behandeln des Reaktionsprodukts mit Aethanol. Beranek et al.; Collection of Czechoslovak Chemical Communications; vol. 19; (1954); p. 1231,1236 View in Reaxys
Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
8/12
2017-11-06 12:48:25
O
Cl
O
O
O
Cl
O
Cl
Cl
O
O O
O
O
O
O
O
O O
O O
O
Rx-ID: 656131 View in Reaxys 21/36 Yield
Conditions & References anschliessenden Erwaermen mit Aethanol Beranek et al.; Collection of Czechoslovak Chemical Communications; vol. 19; (1954); p. 1231,1236 View in Reaxys
O O– Na +
O
O
O O
O
HO O
O
O
O
O
O O
O O
O
Rx-ID: 726701 View in Reaxys 22/36 Yield
Conditions & References Schulz; ; (1940); p. 53; ; (1942); p. 7015 View in Reaxys HO
O O
O
O O
O
O
O
O
O O
O
O O
O
O
Rx-ID: 726702 View in Reaxys 23/36 Yield
Conditions & References With ethanol, sodium ethanolate Schulz; ; (1940); p. 51,53 View in Reaxys O O
O O
O
O
O O
O
Rx-ID: 248575 View in Reaxys 24/36 Yield
Conditions & References bei der Ozonspaltung Malachowski; Czornodola; Chemische Berichte; vol. 68; (1935); p. 369 View in Reaxys O O
itaconic acid ethyl ester
O O
O
Rx-ID: 6190300 View in Reaxys 25/36 Yield
Conditions & References Ozonolyse Malachowski; Czornodola; Chemische Berichte; vol. 68; (1935); p. 369 View in Reaxys
Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
9/12
2017-11-06 12:48:25
O OO O
O
(v4)
N
E
O
O
O
O
O O
O O
O
O
O
oxalcyanoacetic acid diethyl ester
O O
O
Rx-ID: 7083923 View in Reaxys 26/36 Yield
Conditions & References man erhaelt der Oxalessigester infolge des α-Cyan-aconitsaeure-triaethylester-Gehalts Desai; Journal of the Chemical Society; (1932); p. 1079,1086 View in Reaxys
O
O– Na +
OH
O
O
O
O
O
O O
oxalcitric acid lactonetriethyl ester
O O
O
α-pyrone-tricarboxylic acid-(4.5.6)-triethyl ester Rx-ID: 6217821 View in Reaxys 27/36
Yield
Conditions & References Gault; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 158; (1914); p. 713; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 159; (1914); p. 74 View in Reaxys
O
O
O
O
O
sodium
O
O
O
O
oxalcitric acid lactonetriethyl ester
O O
O
α-pyrone-tricarboxylic acid-(4.5.6)-triethyl ester Rx-ID: 6217822 View in Reaxys 28/36
Yield
Conditions & References Gault; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 158; (1914); p. 713; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 159; (1914); p. 74 View in Reaxys
O
Cl
H
O
HN O
O
E N
O O
H 2N
O
NH 2
O
NH
O
O O
EN
O
O
Rx-ID: 7066319 View in Reaxys 29/36 Yield
Conditions & References Mueller,R.; Journal fuer Praktische Chemie (Leipzig); vol. <2>56; (1897); p. 479,480 View in Reaxys
Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
10/12
2017-11-06 12:48:25
O
O
O
E N
HN O
O O
H
N
H 2N
H
H
O
NH 2
O
NH
O
O O
EN
O
O
Rx-ID: 7066320 View in Reaxys 30/36 Yield
Conditions & References Mueller,R.; Journal fuer Praktische Chemie (Leipzig); vol. <2>56; (1897); p. 479,480 View in Reaxys O
O
O
O
OH
O
O
O
O
O O
O
O
Rx-ID: 114921 View in Reaxys 31/36 Yield
Conditions & References Michael; Bucher; Chemische Berichte; vol. 28; (1895); p. 2511; Chemische Berichte; vol. 39; (1906); p. 205 View in Reaxys O
O
O
O OH
O
O
O O
O
O
Rx-ID: 114922 View in Reaxys 32/36 Yield
Conditions & References Michael; Bucher; Chemische Berichte; vol. 28; (1895); p. 2511; Chemische Berichte; vol. 39; (1906); p. 205 View in Reaxys O OH
O
–O
O
O
2
O
O
OH
Cu 2+
H
N
O
H
O
H
NH
O O
O
Rx-ID: 7066317 View in Reaxys 33/36 Yield
Conditions & References Thomas-Mamert; Bulletin de la Societe Chimique de France; vol. <3>11; (1894); p. 482; Bulletin de la Societe Chimique de France; vol. <3>13; (1895); p. 850 View in Reaxys
O
O– Na +
O
O
O
O
O
O
O O
O O
O
Rx-ID: 646770 View in Reaxys 34/36 Yield
Conditions & References Wislicenus; Chemische Berichte; vol. 19; (1886); p. 3225; Justus Liebigs Annalen der Chemie; vol. 246; (1888); p. 315 View in Reaxys
OH
O– Na +
O
O
O
O O
O O
O
O O
O
Rx-ID: 646771 View in Reaxys 35/36
Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
11/12
2017-11-06 12:48:25
Yield
Conditions & References Wislicenus; Chemische Berichte; vol. 19; (1886); p. 3225; Justus Liebigs Annalen der Chemie; vol. 246; (1888); p. 315 View in Reaxys
O
O
O
O O
sodium
O
O O
O
O O
O
Rx-ID: 6190302 View in Reaxys 36/36 Yield
Conditions & References Wislicenus; Chemische Berichte; vol. 19; (1886); p. 3225; Justus Liebigs Annalen der Chemie; vol. 246; (1888); p. 315 View in Reaxys
Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
12/12
2017-11-06 12:48:25