N-Hydroxy-1-phenyl-2-propanimine (1-Phenylpropan-2-one oxime) [C9H11NO]

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37 reactions in Reaxys

2017-12-12 00h:17m:52s (EST)

37 reactions in Reaxys

2017-12-12 00h:19m:36s (EST)

N OH

1. Query

Search as: As drawn 2. Query

(1. Query) AND NOT itemno in (7,6,5)

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O O

N

HO

N

Rx-ID: 1040193 View in Reaxys 1/37 Yield 94 %

Conditions & References With hydrogen in ethanol, Time= 0.333333h, T= 60 °C , p= 15001.5Torr , Autoclave, chemoselective reaction Ren, Yujing; Wei, Haisheng; Yin, Guangzhao; Zhang, Leilei; Wang, Aiqin; Zhang, Tao; Chemical Communications; vol. 53; nb. 12; (2017); p. 1969 - 1972 View in Reaxys

91 %

With sulfuric acid in water, isopropyl alcohol, T= 10 - 15 °C , electrolysis Wessling, Michael; Schaefer, Hans J.; Chemische Berichte; vol. 124; nb. 10; (1991); p. 2303 - 2306 View in Reaxys

82 %

With sodium stannite in tetrahydrofuran, water, Time= 0.416667h, Ambient temperature Varma, Rajender S.; Varma, Manju; Kabalka, George W.; Tetrahedron Letters; vol. 26; nb. 49; (1985); p. 6013 6014 View in Reaxys

81 %

With zinc(II) tetrahydroborate in DME, Time= 6h, Ambient temperature Ranu, Brindaban C.; Chakraborty, Rupak; Tetrahedron Letters; vol. 32; nb. 29; (1991); p. 3579 - 3582 View in Reaxys

81 %

With zinc(II) tetrahydroborate in DME, Time= 6h, T= 25 °C Ranu; Chakraborty; Tetrahedron; vol. 48; nb. 25; (1992); p. 5317 - 5322 View in Reaxys

81 %

With zinc(II) tetrahydroborate in DME, Time= 6h, Ambient temperature, other α-substituted nitroalkenes Ranu, Brindaban C.; Chakraborty, Rupak; Tetrahedron Letters; vol. 32; nb. 29; (1991); p. 3579 - 3582 View in Reaxys

81 %

With zinc(II) tetrahydroborate in DME, Time= 6h, T= 25 °C , other disubstituted nitroalkenes, Mechanism Ranu; Chakraborty; Tetrahedron; vol. 48; nb. 25; (1992); p. 5317 - 5322 View in Reaxys

67 %

With sodium hypophosphite, palladium on activated charcoal in tetrahydrofuran, Time= 3h, Ambient temperature Varma, Rajender S.; Varma, Manju; Kabalka, George W.; Synthetic Communications; vol. 16; nb. 1; (1986); p. 91 - 96 View in Reaxys With hydrogenchloride, tin(ll) chloride in methanol, T= -5 °C Dornow,A.; Mueller,A.; Chemische Berichte; vol. 93; (1960); p. 32 - 40 View in Reaxys

O

HO

N

Rx-ID: 780138 View in Reaxys 2/37 Yield 81 %

Conditions & References With hydroxylamine hydrochloride, sodium carbonate in ethanol, water, Time= 24h, Heating Langhals, Heinz; Range, Guenter; Wistuba, Eckehardt; Ruechardt, Christoph; Chemische Berichte; vol. 114; nb. 12; (1981); p. 3813 - 3830 View in Reaxys

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80 %

With hydroxylamine hydrochloride, silica gel, tert-butanol, Time= 0.183333h Kiasat, Ali Reza; Kazemi, Foad; Nourbakhsh, Kazem; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 179; nb. 6; (2004); p. 1193 - 1196 View in Reaxys

80 %

2. General procedure for preparation of oximes from aldehydes and ketones in the presence of ZnO nanotubes under solvent free condition General procedure: Hydroxylamine hydrochloride (0.138 g, 2 mmol), ZnO nanotubes (0.071 g, 0.8 mmol), silica gel (0.43 g) and aldehyde (ketone) (1 mmol) were ground together in a mortar with a pestle at room temperature for a period of time as indicated in Tables 1 and 2. The progress of the reaction was monitored by TLC. After complete disappearance of the starting materials, the reaction mixture was poured with diethyl ether (2×10 mL) and filtered to remove silica gel and ZnO nanotubes, The filtrate mixed with water and extracted. The solvent was removed in vaccuo to give the product which was recrystallized from suitable solvent and afforded the TLC and 1H-NMR pure products in 75-98 percent isolated yields. With Zincite, hydroxylamine hydrochloride, silica gel in neat (no solvent), Time= 0.05h, T= 20 °C , Green chemistry Kiasat, Ali Reza; Javaherian, Mohammad; Daei, Mina; Farbod, Mansoor; Revue Roumaine de Chimie; vol. 60; nb. 9; (2015); p. 875 - 880 View in Reaxys

47 %

With hydroxylamine hydrochloride, sodium acetate in ethanol, Time= 4h, T= 20 °C Portela-Cubillo, Fernando; Lymer, James; Scanlan, Eoin M.; Scott, Jackie S.; Walton, John C.; Tetrahedron; vol. 64; nb. 52; (2008); p. 11908 - 11916 View in Reaxys

18 %

With hydroxylamine hydrochloride, sodium hydroxide in ethanol, water, Time= 1h, Reflux Yamamoto, Yutaro; Hasegawa, Hiroto; Yamataka, Hiroshi; Journal of Organic Chemistry; vol. 76; nb. 11; (2011); p. 4652 - 4660 View in Reaxys With ethanol, hydroxylamine hydrochloride, sodium carbonate Kolb; Justus Liebigs Annalen der Chemie; vol. 291; (1896); p. 267 View in Reaxys Dollfus; Chemische Berichte; vol. 25; (1892); p. 1918; Chemische Berichte; vol. 26; (1893); p. 1971 View in Reaxys With ethanol, hydroxylamine hydrochloride, water, sodium acetate Neber; v. Friedolsheim; Justus Liebigs Annalen der Chemie; vol. 449; (1926); p. 129 View in Reaxys With sodium hydroxide, hydroxylamine hydrochloride Hey; Journal of the Chemical Society; (1930); p. 18,20 View in Reaxys With sodium hydroxide, hydroxylamine in water, Time= 0.25h, Yield given Lozynski, Marek; Rusinska-Roszak, Danuta; Polish Journal of Chemistry; vol. 60; nb. 4-6; (1986); p. 625 - 630 View in Reaxys With pyridine, hydroxylamine hydrochloride in ethanol, Heating, Condensation Katritzky, Alan R.; Cui, Xilin; Long, Qiuhe; Yang, Baozhen; Wilcox, Allan L.; Zhang, Yong-Kang; Organic Preparations and Procedures International; vol. 32; nb. 2; (2000); p. 175 - 183 View in Reaxys With hydroxylamine hydrochloride, sodium acetate in methanol, water, T= 20 °C Xuan, Jun; Xia, Xu-Dong; Zeng, Ting-Ting; Feng, Zhu-Jia; Chen, Jia-Rong; Lu, Liang-Qiu; Xiao, Wen-Jing; Angewandte Chemie - International Edition; vol. 53; nb. 22; (2014); p. 5653 - 5656; Angew. Chem.; vol. 126; nb. 22; (2014); p. 5759 - 5762,4

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View in Reaxys O N

H

HO

N

O

O

O

N O

Rx-ID: 41124386 View in Reaxys 3/37 Yield

Conditions & References Reaction Steps: 2 1: N-butylamine / ethanol / |Reflux 2: acetic acid; tetraethylammonium tetrafluoroborate / DMFA; water / 20 °C / |Electrolysis With tetraethylammonium tetrafluoroborate, acetic acid, N-butylamine in ethanol, water, DMFA Wessling, Michael; Schäfer, Hans J.; Beilstein Journal of Organic Chemistry; vol. 11; (2015); p. 1163 - 1174 View in Reaxys O

O O

N

N

E

HO

N

O

O

N O

Rx-ID: 41124393 View in Reaxys 4/37 Yield 20 %, 24 %

Conditions & References Electrolyses General procedure: The cathodic hydrodimerization is performed based on the results of the experiments shown in Tables 1 and 2 (Theoretical part) in an undivided cell (Figure 1a without diaphragm) at a mercury pool cathode at T = 0 °C (outside cooling). Electrolyte was a 0.2 M solution of tetraethylammonium p-toluenesulfonate (TEA-pTos) in DMF. The supporting electrolyte contained 2 percent water, is hygroscopic and was not dried. DMF is also not dried. To remove free amines the solvent was purged for some time with dry nitrogen gas. The supporting electrolyte is purged before the electrolyis for 10 min with nitrogen to remove dissolved oxygen. The given amount of substrate dissolved in 20 mL supporting electrolyte is given into the cell. The Luggin capillary is filled with electrolyte and positioned close to the cathode. Subsequently the anode is placed in the cell with a distance of 1 cm to the mercury surface. It is secured that in spite of the small distance to the cathode stirring of the mercury pool (500 t/min) can be done without disturbances of the current flow. Under argon the solution of the olefin is electrolyzed at the given potential until the current has decreased to 1–10 mA (istart = 250–450 mA). During the reduction – especially when stirring is stopped – at the cathode a deep colouring of the solution being red, brown or violet depending on the olefin can be observed. It diffuses into the solution and is discoloured at the anode. In the course of the electrolysis this leads to the colouring of the electrolyte. With tetraethylammonium tetrafluoroborate, acetic acid in water, DMFA, T= 20 °C , Electrolysis, Concentration Wessling, Michael; Schäfer, Hans J.; Beilstein Journal of Organic Chemistry; vol. 11; (2015); p. 1163 - 1174 View in Reaxys

O

O

OH

N

NZ

HO

NE

Rx-ID: 1986968 View in Reaxys 5/37 Yield

Conditions & References With tin(ll) chloride in acetone, Time= 0.75h, Ambient temperature, Yield given. Yields of byproduct given. Title compound not separated from byproducts Varma, Rajender S.; Varma, Manju; Gai, Yuan-Zhu; Kabalka, George W.; Heterocycles; vol. 24; nb. 9; (1986); p. 2581 - 2586 View in Reaxys

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With chromium dichloride, hydrogenchloride in tetrahydrofuran, Time= 0.166667h, Yield given. Yields of byproduct given. Title compound not separated from byproducts Varma, Rajender S.; Varma, Manju; Kabalka, George W.; Synthetic Communications; vol. 15; nb. 14; (1985); p. 1325 - 1332 View in Reaxys With sodium hydrogencarbonate, tin(ll) chloride, 1.) acetone, RT, 45 min, 2.) acetone, pH=8, 15 min, Yield given. Multistep reaction. Yields of byproduct given Varma, Rajender S.; Varma, Manju; Gai, Yuan-Zhu; Kabalka, George W.; Heterocycles; vol. 24; nb. 9; (1986); p. 2581 - 2586 View in Reaxys Reduction of Nitroalkenes to Oximes 2; General Procedure15 General procedure: To a dry three-necked flask was charged nitroalkene (80 mmol), dryammonium formate (25.2 g, 400 mmol) and MeOH–toluene (1:1, 200 mL). Pd/C (9.5 g, 5 molpercent, wet) was added to the solution under stirring. The resulting mixture was stirred at r.t. until the complete disappearance of the starting material. The mixture was filtered and the filter cake was washed with CH2Cl2 (50 mL). The combined filtrates were concentrated, retreated with CH2Cl2 (50 mL), filtered to remove the insoluble salt, and concentrated. The residue was purified by column chromatography (silica gel, hexanes–EtOAc, 15:1) to afford the desired product as a mixture of E/Z isomers (E/Z 0.8:1 to 2.8:1). With 5 palladium on charcoal, ammonium formate in methanol, toluene, T= 20 °C , Inert atmosphere, Overall yield = 72 percent; Overall yield = 8.6 g Cai, Zhihua; Liu, Guodu; Jiao, Guangjun; Senanayake, Chris H.; Tang, Wenjun; Synthesis (Germany); vol. 45; nb. 24; (2013); p. 3355 - 3360; Art.No: SS-2013-H0581-OP View in Reaxys

HO

N

Rx-ID: 37546659 View in Reaxys 6/37 Yield

Conditions & References

53 %

With hydroxylamine in water, isopropyl alcohol, T= 140 °C Loiseau, Francis; Beauchemin, Andre M.; Organic Syntheses; vol. 90; (2013); p. 87 - 95 View in Reaxys

O O

N

O E

O

N

HO

N

Rx-ID: 32288948 View in Reaxys 7/37 Yield

Conditions & References With glucose-6-phosphate dehydrogenase, G-6-P, wild type pentaerythritol tetranitrate reductase, NADPH in N,Ndimethyl-formamide, Time= 4h, T= 30 °C , phosphate buffer, Inert atmosphere, anaerobic, Enzymatic reaction, enantioselective reaction Toogood, Helen S.; Fryszkowska, Anna; Hulley, Martyn; Sakuma, Michiyo; Mansell, David; Stephens, Gill M.; Gardiner, John M.; Scrutton, Nigel S.; ChemBioChem; vol. 12; nb. 5; (2011); p. 738 - 749 View in Reaxys

O O

N

O O

N

HO

N

Rx-ID: 29629445 View in Reaxys 8/37

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Yield 41 %, 10 %

Conditions & References With palladium 10 on activated carbon, hydrogen in methanol, Time= 0.666667h, T= 20 °C Durchschein, Katharina; Ferreira-Da Silva, Bianca; Wallner, Silvia; MacHeroux, Peter; Kroutil, Wolfgang; Glueck, Silvia Maria; Faber, Kurt; Green Chemistry; vol. 12; nb. 4; (2010); p. 616 - 619 View in Reaxys

HO

N

Rx-ID: 28612839 View in Reaxys 9/37 Yield 71 %

Conditions & References With hydroxylamine in water, isopropyl alcohol, Time= 18.0833h, T= 110 °C , Inert atmosphere, regioselective reaction Moran, Joseph; Pfeiffer, Jennifer Y.; Gorelsky, Serge I.; Beauchemin, Andre M.; Organic Letters; vol. 11; nb. 9; (2009); p. 1895 - 1898 View in Reaxys

HO HO

N

E N

Rx-ID: 28003517 View in Reaxys 10/37 Yield 5 %, 53 %

Conditions & References With hydroxylamine in isopropyl alcohol, Time= 10h, T= 140 °C , microwave irradiation, intermolecular Cope-type hydroamination Beauchemin, Andre M.; Moran, Joseph; Lebrun, Marie-Eve; Seguin, Catherine; Dimitrijevic, Elena; Zhang, Lili; Gorelsky, Serge I.; Angewandte Chemie - International Edition; vol. 47; nb. 8; (2008); p. 1410 - 1413 View in Reaxys

HO HO

N

N

Rx-ID: 28495641 View in Reaxys 11/37 Yield 53 %, 5 %

Conditions & References With hydroxylamine in water, isopropyl alcohol, T= 140 °C , Microwave irradiation, Inert atmosphere, Cope-type hydroamination, regioselective reaction Moran, Joseph; Gorelsky, Serge I.; Dimitrijevic, Elena; Lebrun, Marie-Eve; Bedard, Anne-Catherine; Seguin, Catherine; Beauchemin, Andre M.; Journal of the American Chemical Society; vol. 130; nb. 52; (2008); p. 17893 17906 View in Reaxys OH

O

NZ

HO

NE

Rx-ID: 10065898 View in Reaxys 12/37 Yield 5 %, 90 %

Conditions & References With hydroxylamine hydrochloride, iron(III) chloride, Time= 0.333333h, T= 50 °C Eshghi, Hossein; Hassankhani, Asadollah; Organic Preparations and Procedures International; vol. 37; nb. 6; (2005); p. 575 - 579 View in Reaxys With hydroxylamine hydrochloride, sodium carbonate in tetrahydrofuran, water, Time= 2h, Title compound not separated from byproducts

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Cashman, John R.; Xiong, Yeng N.; Lifen, Xu; Janowsky, Aaron; Journal of Pharmacology and Experimental Therapeutics; vol. 288; nb. 3; (1999); p. 1251 - 1260 View in Reaxys OH

Z

O

N

NZ

HO

NE

O

Rx-ID: 8621051 View in Reaxys 13/37 Yield

Conditions & References With indium, ammonium chloride in methanol, Time= 3h, Heating, Reduction, Title compound not separated from byproducts Yadav; Subba Reddy; Srinivas; Ramalingam; Synlett; nb. 10; (2000); p. 1447 - 1449 View in Reaxys

O O

N

HO

N

Rx-ID: 5144276 View in Reaxys 14/37 Yield 67 %

Conditions & References With n-butyllithium, hexamethyl-silane in tetrahydrofuran, hexane, Time= 24h, Ambient temperature Hwu, Jih Ru; Tseng, Wen Nan; Patel, Himatkumar V.; Wong, Fong Fuh; Horng, Den-Nan; Liaw, Ben Ruey; Lung Ching, Lin; Journal of Organic Chemistry; vol. 64; nb. 7; (1999); p. 2211 - 2218 View in Reaxys

O

H 2N N

N

HO

N

O

Rx-ID: 3984410 View in Reaxys 15/37 Yield 50 % Spectr., 50 % Spectr.

Conditions & References With oxaziridinium tetrafluoroborate derived from N-methyl-1,2,3,4-tetrahydroisoquinoline in dichloromethane, Time= 0.25h, T= 0 °C Hanquet, Gilles; Lusinchi, Xavier; Tetrahedron; vol. 50; nb. 42; (1994); p. 12185 - 12200 View in Reaxys

H

HO

N

O

Rx-ID: 20915506 View in Reaxys 16/37 Yield

Conditions & References Reaction Steps: 2 1: n-BuNH2 / ethanol / Heating; or HOAc, NH4OAc 2: 91 percent / 0.1 M H2SO4 / propan-2-ol; H2O / 10 - 15 °C / electrolysis With sulfuric acid, N-butylamine in ethanol, water, isopropyl alcohol Wessling, Michael; Schaefer, Hans J.; Chemische Berichte; vol. 124; nb. 10; (1991); p. 2303 - 2306 View in Reaxys

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O N

O

E

HO

N

Rx-ID: 1553469 View in Reaxys 17/37 Yield

Conditions & References

94 %

With ammonium formate, palladium on activated charcoal in tetrahydrofuran, methanol, Time= 0.33h, Ambient temperature Kabalka, George W.; Pace, R. David; Wadgaonkar, P.P.; Synthetic Communications; vol. 20; nb. 16; (1990); p. 2453 - 2458 View in Reaxys

O

Br

E

N

N

HO

HO

N

Br

O

Rx-ID: 2153011 View in Reaxys 18/37 Yield

Conditions & References

34 %, 35 %

With ammonium formate, palladium on activated charcoal in tetrahydrofuran, methanol, Time= 2.5h, Ambient temperature Kabalka, George W.; Pace, R. David; Wadgaonkar, P.P.; Synthetic Communications; vol. 20; nb. 16; (1990); p. 2453 - 2458 View in Reaxys

O O

N

E

HO

N

O

Rx-ID: 1553470 View in Reaxys 19/37 Yield

Conditions & References

85 %, 4 %

With sodium dithionite, 1,1'-di-n-octyl-4,4'-bipyridinium dibromide in water, ethyl acetate, Time= 1h Tomioka, Hideo; Ueda, Koichi; Ohi, Hirofumi; Izawa, Yasuji; Chemistry Letters; (1986); p. 1359 - 1362 View in Reaxys

O

HO

N

HO

N

Rx-ID: 1554138 View in Reaxys 20/37 Yield

Conditions & References

79 %

With sodium hydroxide, hydroxylamine in water, isopropyl alcohol, Time= 1h, Ambient temperature Lozynski, Marek; Rusinska-Roszak, Danuta; Polish Journal of Chemistry; vol. 60; nb. 4-6; (1986); p. 625 - 630 View in Reaxys

O

HO

N HO

N

Rx-ID: 1716247 View in Reaxys 21/37 Yield 3%

Conditions & References With sodium hydroxide, hydroxylamine, tert-butylamine hydrochloride in water, isopropyl alcohol, Time= 2h, T= 80 °C Lozynski, Marek; Rusinska-Roszak, Danuta; Polish Journal of Chemistry; vol. 60; nb. 4-6; (1986); p. 625 - 630 View in Reaxys

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O

Br

N

HO

HO

N

N Br

O

Rx-ID: 2070996 View in Reaxys 22/37 Yield

Conditions & References

40 %, 30 %

With sodium hypophosphite, palladium on activated charcoal in tetrahydrofuran, Time= 0.5h, Ambient temperature Varma, Rajender S.; Varma, Manju; Kabalka, George W.; Synthetic Communications; vol. 16; nb. 1; (1986); p. 91 - 96 View in Reaxys

HO O

N

N

OH

Rx-ID: 3935132 View in Reaxys 23/37 Yield

Conditions & References

57 %

With sodium hydroxide, hydroxylamine in water, isopropyl alcohol, Time= 0.25h, Ambient temperature Lozynski, Marek; Rusinska-Roszak, Danuta; Polish Journal of Chemistry; vol. 60; nb. 4-6; (1986); p. 625 - 630 View in Reaxys

O N

O

N

HO

O

Rx-ID: 1986971 View in Reaxys 24/37 Yield

Conditions & References

43 %, 6 %

With sulfuric acid, toluene-4-sulfonic acid in methanol, T= 0 - 5 °C , ceramic diaphragm, carbon-rod anode, platinum cathode, 4.5 F/mol, 0.1A, cathode potential -1.45 to -1.65V vs. SCE Shono, Tatsuya; Hamaguchi, Hiroshi; Mikami, Hiroshi; Nogusa, Hideo; Kashimura, Shigenori; Journal of Organic Chemistry; vol. 48; nb. 12; (1983); p. 2103 - 2105 View in Reaxys

Z N

O

HO

N

O

Rx-ID: 2125434 View in Reaxys 25/37 Yield 75 %

Conditions & References With hydroxylamine hydrochloride, sodium acetate in 1,4-dioxane, perchloric acid, dichloromethane, Time= 2h, Ambient temperature Torii, Sigeru; Tanaka, Hideo; Katoh, Tetsuo; Chemistry Letters; (1983); p. 607 - 610 View in Reaxys OH

HO

NE

NZ

Rx-ID: 2102946 View in Reaxys 26/37 Yield 36 %

Conditions & References in nitrobenzene, Time= 1h, T= 150 °C , other temperature, other solvent (DMSO), KOH, Product distribution Trofimov, B. A.; Korostova, S. E.; Sobenina, L. N.; Mikhaleva, A. I.; Bzhezovskii, V. M.; et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 18; nb. 2; (1982); p. 148 - 152; Khimiya Geterotsiklicheskikh Soedinenii; vol. 18; nb. 2; (1982); p. 193 - 198

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View in Reaxys OH NZ

Rx-ID: 7247825 View in Reaxys 27/37 Yield

Conditions & References Phenylaceton , H2NOH Alvernhe; Laurent; Bulletin de la Societe Chimique de France; (1970); p. 3003,3004,3007 View in Reaxys Phenylpropan-2-on, NH2OH, Pyridin, wss.NaOH (neben d. anti-Isomeren) Huitric et al.; Journal of Organic Chemistry; vol. 32; (1967); p. 1661 View in Reaxys N-Hydroxyamphetamin, Autoxid. Lindeke et al.; Acta Pharmaceutica Suecica; vol. 12; (1975); p. 183,192, 193 View in Reaxys N-Hydroxyphentermin, Autoxid. Lindeke et al.; Acta Pharmaceutica Suecica; vol. 12; (1975); p. 183,192, 193 View in Reaxys

HO

NE

Rx-ID: 7362548 View in Reaxys 28/37 Yield

Conditions & References Phenylpropan-2-on, NH2OH, Pyridin, wss.NaOH (neben d. syn-Isomeren) Huitric et al.; Journal of Organic Chemistry; vol. 32; (1967); p. 1661 View in Reaxys entspr. Keton, NH2OH Foreman; Siegel; Mrtek; Journal of pharmaceutical sciences; vol. 58; nb. 2; (1969); p. 189 - 192 View in Reaxys N-Hydroxyamphetamin, Autoxid. Lindeke et al.; Acta Pharmaceutica Suecica; vol. 12; (1975); p. 183,192, 193 View in Reaxys N-Hydroxyphentermin, Autoxid. Lindeke et al.; Acta Pharmaceutica Suecica; vol. 12; (1975); p. 183,192, 193 View in Reaxys

HO

N

Rx-ID: 5856922 View in Reaxys 29/37 Yield

Conditions & References Phenylaceton , H2NOH Alvernhe; Laurent; Bulletin de la Societe Chimique de France; (1970); p. 3003,3004,3007

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View in Reaxys N-Hydroxy-N-n-propylamphetamin Ie, W., gelbes Quecksilberoxyd Beckett; Coutts; Ogunbona; Journal of Pharmacy and Pharmacology; vol. 26; nb. 5; (1974); p. 312 - 316 View in Reaxys N-Aethyl-N-hydroxyamphetamin Id, W., gelbes Quecksilberoxyd Beckett; Coutts; Ogunbona; Journal of Pharmacy and Pharmacology; vol. 26; nb. 5; (1974); p. 312 - 316 View in Reaxys 8a, Chloroperbenzoesaeure, LiAlH4 (u. Homologe) Beckett; Coutts; Ogunbona; Tetrahedron; vol. 29; nb. 24; (1973); p. 4189 - 4193 View in Reaxys

Cl

Cl HO

HO

N

N

Rx-ID: 1048770 View in Reaxys 30/37 Yield

Conditions & References With hydrogenchloride, nitrosylchloride, Time= 9h, T= 20 °C , Irradiation, Further byproducts given Julliard,M.; Bulletin de la Societe Chimique de France; (1970); p. 2001 - 2004 View in Reaxys Cl

HO

N

N

HO

Rx-ID: 1125567 View in Reaxys 31/37 Yield

Conditions & References With hydrogen, palladium on activated charcoal in methanol Biela,R. et al.; Journal fuer Praktische Chemie (Leipzig); vol. 33; (1966); p. 282 - 292 View in Reaxys

HO

N

Rx-ID: 22423453 View in Reaxys 32/37 Yield

Conditions & References Reaction Steps: 2 1: NOCl, HCl / diethyl ether 2: H2 / Pd-C / methanol With hydrogenchloride, hydrogen, nitrosyl chloride, palladium on activated charcoal in methanol, diethyl ether Biela,R. et al.; Journal fuer Praktische Chemie (Leipzig); vol. 33; (1966); p. 282 - 292 View in Reaxys O

–O

S O

O

N

K+

HO

aqueous acids

N

Rx-ID: 8255750 View in Reaxys 33/37 Yield

Conditions & References Smith; Journal of the American Chemical Society; vol. 70; (1948); p. 320,322; Journal of the American Chemical Society; vol. 76; (1954); p. 436,441

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View in Reaxys

HO

2-nitro-1-phenyl-propene-(1)

N

Rx-ID: 5856923 View in Reaxys 34/37 Yield

Conditions & References With hydrogenchloride, iron, weiteres Reagens: FeCl3 Patent; Purdue Research Found.; US2233823; (1939) View in Reaxys With hydrogenchloride, iron, weiteres Reagens: FeCl3 Patent; Purdue Research Found.; US2233823; (1939) View in Reaxys

HO

N

HO

N Cl

H

Rx-ID: 668824 View in Reaxys 35/37 Yield

Conditions & References With hydrogenchloride, diethyl ether Dollfus; Chemische Berichte; vol. 25; (1892); p. 1918; Chemische Berichte; vol. 26; (1893); p. 1971 View in Reaxys

O

HO

hydroxylamine solution

N

Rx-ID: 5856924 View in Reaxys 36/37 Yield

Conditions & References With ethanol Dollfus; Chemische Berichte; vol. 25; (1892); p. 1918; Chemische Berichte; vol. 26; (1893); p. 1971 View in Reaxys

O

HO

N Cl

H

Rx-ID: 22069718 View in Reaxys 37/37 Yield

Conditions & References Reaction Steps: 2 1: alcohol 2: absolute diethyl ether; HCl With hydrogenchloride, diethyl ether, ethanol Dollfus; Chemische Berichte; vol. 25; (1892); p. 1918; Chemische Berichte; vol. 26; (1893); p. 1971 View in Reaxys Reaction Steps: 2 1: sodium carbonate; aqueous alcohol; hydroxylamine hydrochloride 2: absolute diethyl ether; HCl With hydrogenchloride, diethyl ether, ethanol, hydroxylamine hydrochloride, sodium carbonate Dollfus; Chemische Berichte; vol. 25; (1892); p. 1918; Chemische Berichte; vol. 26; (1893); p. 1971 View in Reaxys

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2017-12-12 00:41:47


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.

13/13

2017-12-12 00:41:47


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