2. Alkyl-NH2 to Alkyl=N-OH [Reaxys, Reactions (29); 2016-03-07]

Query Query

Results

Date

29 reactions in Reaxys

2016-03-07 12h:24m:37s (EST)

OH

1. Query

NH 2

N

ALK ALK

Search as: As drawn, No salts, No mixtures

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OH

NH 2

H

EN

Rx-ID: 39176249 View in Reaxys 1/29 Yield

Conditions & References

38 %

General procedure for the aerobic oxidative synthesis of oximes General procedure: A mixture of 2 mmol primary amine, acetaldoxime (6.2 mmol),InCl3 (0.1 mmol), TEMPO (0.2 mmol), and Toluene (10 ml) was placed in a 20 ml three-necked flasks. O2 was bubbled into the flask at a flow rate of 20 ml/ min. The reaction mixture was stirred at 100 °C for several hours and the reaction progress was monitored by TLC. After cooling to room temperature, the solution was directly evaporated to dryness and the residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane = 1:8)to give the corresponding oximes.

With indium(III) chloride, acetaldehyde oxime, 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical, oxygen in toluene, Time= 12h, T= 100 °C Yu, Jiatao; Cao, Xiaohua; Lu, Ming; Tetrahedron Letters; vol. 55; nb. 42; (2014); p. 5751 - 5755 View in Reaxys

OH

NH 2

N

Rx-ID: 28151343 View in Reaxys 2/29 Yield

Conditions & References

82 %

With diperoxydodecanedioic acid in DMFA, Time= 0.333333h, T= 20 - 55 °C Patil, Vilas V.; Gayakwad, Eknath M.; Shankarling, Ganapati S.; New Journal of Chemistry; vol. 39; nb. 8; (2015); p. 6677 - 6682 View in Reaxys

73 %Chromat.

With WO3, aluminum oxide, 2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazyl, oxygen in acetonitrile, Time= 36h, T= 80 °C , p= 37503.8Torr Suzuki, Ken; Watanabe, Tomonari; Murahashi, Shun-Ichi; Angewandte Chemie - International Edition; vol. 47; nb.

11; (2008); p. 2079 - 2081 View in Reaxys

73 %Chromat.

With tungusten oxide/alumina, oxygen, DPPH-H in acetonitrile, Time= 36h, T= 80 °C , p= 37503.8Torr Suzuki, Ken; Watanabe, Tomonari; Murahashi, Shun-Ichi; Journal of Organic Chemistry; vol. 78; nb. 6; (2013); p.

2301 - 2310 View in Reaxys

OH

NH 2

N

Rx-ID: 686793 View in Reaxys 3/29 Yield 82 %

Conditions & References With diperoxydodecanedioic acid in DMFA, Time= 0.333333h, T= 20 - 55 °C Patil, Vilas V.; Gayakwad, Eknath M.; Shankarling, Ganapati S.; New Journal of Chemistry; vol. 39; nb. 8; (2015); p. 6677 - 6682

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View in Reaxys 74 %

With hydrogen peroxide, Titanium(IV) oxide in methanol, Time= 6h, T= 60 °C Kidwai, Mazaahir; Bhardwaj, Saurav; Synthetic Communications; vol. 41; nb. 18; (2011); p. 2655 - 2662 View in Reaxys With sodium tungstate, water, hydrogen peroxide Patent; Inventa A.G.; DE939808; (1952) View in Reaxys With sodium tungstate, hydrogen peroxide in ethanol Kahr,K.; Berther,C.; Chemische Berichte; vol. 93; (1960); p. 132 - 136 View in Reaxys OH N

NH 2

O N

N

N

N

O

O

Rx-ID: 5052036 View in Reaxys 4/29 Yield 47 %, 11 %, 38 %

Conditions & References With dihydrogen peroxide, methyltrioxorhenium (VII) in tert-butyl alcohol, Time= 0.5h, T= 20 °C , Oxidation Yamazaki, Shigekazu; Bulletin of the Chemical Society of Japan; vol. 70; nb. 4; (1997); p. 877 - 883 View in Reaxys

43 %, 20 %, 40 %

With dihydrogen peroxide, methyltrioxorhenium (VII) in acetonitrile, Time= 0.5h, T= 20 °C , Oxidation Yamazaki, Shigekazu; Bulletin of the Chemical Society of Japan; vol. 70; nb. 4; (1997); p. 877 - 883 View in Reaxys OH N NH 2

Rx-ID: 1906314 View in Reaxys 5/29 Yield 78 %

Conditions & References With dihydrogen peroxide, Titanium(IV) oxide in methanol, Time= 10h, T= 60 °C Kidwai, Mazaahir; Bhardwaj, Saurav; Synthetic Communications; vol. 41; nb. 18; (2011); p. 2655 - 2662 View in Reaxys

72 % Chro- With dihydrogen peroxide, peroxotungstophosphate in tert-butyl alcohol, Time= 5h, Ambient temperature mat.

Sakaue, Shigeki; Sakata, Yasuyuki; Nishiyama, Yutaka; Ishii, Yasutaka; Chemistry Letters; (1992); p. 289 - 292 View in Reaxys

Copyright © 2016 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.

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OH N NH 2

Rx-ID: 31167451 View in Reaxys 6/29 Yield

Conditions & References

78 %

With dihydrogen peroxide, Titanium(IV) oxide in methanol, Time= 8h, T= 60 °C Kidwai, Mazaahir; Bhardwaj, Saurav; Synthetic Communications; vol. 41; nb. 18; (2011); p. 2655 - 2662 View in Reaxys

OH

NH 2

N

Rx-ID: 40994391 View in Reaxys 7/29 Yield 80 %

Conditions & References With diperoxydodecanedioic acid in DMFA, Time= 0.333333h, T= 20 - 55 °C Patil, Vilas V.; Gayakwad, Eknath M.; Shankarling, Ganapati S.; New Journal of Chemistry; vol. 39; nb. 8; (2015); p. 6677 - 6682 View in Reaxys OH

NH 2

N

O N N O

Rx-ID: 1831818 View in Reaxys 8/29 Yield

Conditions & References

65 %, 27 % With sodium perborate, N,N,N',N'-tetraacetylethylenediamine, sodium hydrogencarbonate in water, ethyl acetate, Time= 2.5h, Ambient temperature Zajac, Walter W.; Darcy, Michael G.; Subong, Amador P.; Buzby, John H.; Tetrahedron Letters; vol. 30; nb. 47; (1989); p. 6495 - 6496 View in Reaxys 27 %, 65 % With sodium perborate, N,N,N',N'-tetraacetylethylenediamine, sodium hydrogencarbonate in water, ethyl acetate, Time= 2.5h, Ambient temperature Zajac, Walter W.; Darcy, Michael G.; Subong, Amador P.; Buzby, John H.; Tetrahedron Letters; vol. 30; nb. 47; (1989); p. 6495 - 6496 View in Reaxys OH

NH 2

N

Rx-ID: 29629443 View in Reaxys 9/29 Yield 83 %

Conditions & References With 3-chloro-benzenecarboperoxoic acid in dichloromethane, Time= 1h

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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

OH

NH 2

N

H N HO

Rx-ID: 8615109 View in Reaxys 10/29 Yield

Conditions & References

84 %, 6 %

With Oxonereg;, silica gel in water, Time= 8h, T= 80 °C , Oxidation, Product distribution, Further Variations: Reagents, reaction time Fields, John D.; Kropp, Paul J.; Journal of Organic Chemistry; vol. 65; nb. 19; (2000); p. 5937 - 5941 View in Reaxys OH

O

NH 2

ZN

OH EN

O N N O N O

Rx-ID: 3523590 View in Reaxys 11/29 Yield

Conditions & References

37 %

With anhydrous potassium sulfate, potassium hydrogensulfate, oxone, sodium hydrogencarbonate in dichloromethane, water, Yields of byproduct given Crandall, Jack K.; Reix, Thierry; Journal of Organic Chemistry; vol. 57; nb. 25; (1992); p. 6759 - 6764 View in Reaxys

OH

NH 2

O

O

N

EN

Z

EN

O

N

N

OH

O

Rx-ID: 3307341 View in Reaxys 12/29 Yield

Conditions & References

27 %

With anhydrous potassium sulfate, potassium hydrogensulfate, oxone, sodium hydrogencarbonate in dichloromethane, water, Yields of byproduct given Crandall, Jack K.; Reix, Thierry; Journal of Organic Chemistry; vol. 57; nb. 25; (1992); p. 6759 - 6764 View in Reaxys

OH

NH 2

O N

EN

O

EN

Z

N OH

Rx-ID: 3307692 View in Reaxys 13/29 Yield

Conditions & References With 3,3-dimethyldioxirane, potassium carbonate in acetone, Yields of byproduct given

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Crandall, Jack K.; Reix, Thierry; Journal of Organic Chemistry; vol. 57; nb. 25; (1992); p. 6759 - 6764 View in Reaxys OH EN

OH

NH 2

ZN

Rx-ID: 1920105 View in Reaxys 14/29 Yield

Conditions & References With anhydrous potassium sulfate, potassium hydrogensulfate, oxone, sodium hydrogencarbonate, triethylamine, 1) acetone, water, 2) hexane, 1 h, reflux, Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts Crandall, Jack K.; Reix, Thierry; Journal of Organic Chemistry; vol. 57; nb. 25; (1992); p. 6759 - 6764 View in Reaxys With anhydrous potassium sulfate, 2KHSO5*HHSO4*K2SO4, sulfuric acid, sodium hydrogencarbonate, triethylamine, 1) acetone, water, 2) hexane, 1 h, reflux, Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts Crandall, Jack K.; Reix, Thierry; Journal of Organic Chemistry; vol. 57; nb. 25; (1992); p. 6759 - 6764 View in Reaxys

OH

NH 2

N

Rx-ID: 682432 View in Reaxys 15/29 Yield

Conditions & References With peroxymonosulfuric acid, magnesium oxide Bamberger; Seligmann; Chemische Berichte; vol. 36; (1903); p. 703 View in Reaxys With sodium tungstate, dihydrogen peroxide Patent; Synthese-Chemie; DE952088; (1956) View in Reaxys Patent; Inventa A.G.; DE939808; (1956) View in Reaxys

OH

NH 2

O

O

N

EN

Z

EN

N OH

O

N O

Rx-ID: 3307340 View in Reaxys 16/29 Yield 20 %

Conditions & References With 3,3-dimethyldioxirane, Yields of byproduct given Crandall, Jack K.; Reix, Thierry; Journal of Organic Chemistry; vol. 57; nb. 25; (1992); p. 6759 - 6764 View in Reaxys

Copyright © 2016 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.

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OH

NH 2

EN

Z

N OH

Rx-ID: 3307698 View in Reaxys 17/29 Yield

Conditions & References With 3,3-dimethyldioxirane, potassium carbonate, triethylamine, 1) acetone, 2) hexane, 1 h, reflux, Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts Crandall, Jack K.; Reix, Thierry; Journal of Organic Chemistry; vol. 57; nb. 25; (1992); p. 6759 - 6764 View in Reaxys

OH

NH 2

N

Rx-ID: 630390 View in Reaxys 18/29 Yield

Conditions & References With peroxymonosulfuric acid Bamberger; Chemische Berichte; vol. 35; (1902); p. 4294; Chemische Berichte; vol. 36; (1903); p. 711 View in Reaxys

OH N

NH 2

Rx-ID: 742655 View in Reaxys 19/29 Yield

Conditions & References With peroxymonosulfuric acid, magnesium oxide Bamberger; Seligmann; Chemische Berichte; vol. 36; (1903); p. 703 View in Reaxys OH NH 2

N

Rx-ID: 772773 View in Reaxys 20/29 Yield

Conditions & References With peroxymonosulfuric acid Bamberger; Seligmann; Chemische Berichte; vol. 35; (1902); p. 4299 View in Reaxys

NH 2

OH N

Rx-ID: 906482 View in Reaxys 21/29 Yield

Conditions & References With sodium tungstate, dihydrogen peroxide Kahr,K.; Berther,C.; Chemische Berichte; vol. 93; (1960); p. 132 - 136 View in Reaxys OH

O

NH 2

Copyright © 2016 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.

ZN

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OH EN

O N N

N

O

O

Rx-ID: 3523591 View in Reaxys 22/29 Yield

Conditions & References With 3,3-dimethyldioxirane, sodium hydrogencarbonate, Yield given. Yields of byproduct given Crandall, Jack K.; Reix, Thierry; Journal of Organic Chemistry; vol. 57; nb. 25; (1992); p. 6759 - 6764 View in Reaxys

N

NH 2

O O

O HN

N O

O

OH

N

N

O

N

O O

N O

Rx-ID: 3305847 View in Reaxys 23/29 Yield

Conditions & References

80 %, 62 % in dichloromethane, 0 deg C, 72 h; 20 deg C, 48 h, Product distribution Makhova, N. N.; Petukhova, V. Yu.; Khmel'nitskii, L. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 31; (1982); p. 1858 - 1862; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 9; (1982); p. 2107 - 2110 View in Reaxys O O

N

NH 2

O O N

OH N

N O

O

N O

Rx-ID: 3305851 View in Reaxys 24/29 Yield

Conditions & References

29 %

in dichloromethane, 0 deg C, 72 h; 20 deg C, 48 h, Product distribution Makhova, N. N.; Petukhova, V. Yu.; Khmel'nitskii, L. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 31; (1982); p. 1858 - 1862; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 9; (1982); p. 2107 - 2110 View in Reaxys

N

NH 2

O O

N O

O

N O

O

OH N

HN

O O

HO

N O NH 2

O N

N

O

O

N

N O

Rx-ID: 3305846 View in Reaxys 25/29 Yield 33.5 %, 64.8 %

Conditions & References in dichloromethane, 0 deg C, 8 d; 20 deg C, 5 d, Product distribution

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Makhova, N. N.; Petukhova, V. Yu.; Khmel'nitskii, L. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 31; (1982); p. 1858 - 1862; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 9; (1982); p. 2107 - 2110 View in Reaxys

NH 2

OH

sulfomonoperoxoic acid

N

magnesia

Rx-ID: 5802595 View in Reaxys 26/29 Yield

Conditions & References Bamberger; Seligmann; Chemische Berichte; vol. 36; (1903); p. 703 View in Reaxys

OH NH 2

sulfomonoperoxoic acid

N

magnesia

Rx-ID: 5802724 View in Reaxys 27/29 Yield

Conditions & References Bamberger; Seligmann; Chemische Berichte; vol. 36; (1903); p. 703 View in Reaxys OH NH 2

O

O N

sulfomonoperoxoic acid

HO

N

N H

N

O

Rx-ID: 5803426 View in Reaxys 28/29 Yield

Conditions & References Produkt 5:Ameisensaeure Bamberger; Seligmann; Chemische Berichte; vol. 35; (1902); p. 4299 View in Reaxys

OH

NH 2

N

sulfomonoperoxoic acid

O

O

N

H N OH

N

O

Rx-ID: 6045919 View in Reaxys 29/29 Yield

Conditions & References Pr. 5: Essigsaeure Bamberger; Chemische Berichte; vol. 35; (1902); p. 4294; Chemische Berichte; vol. 36; (1903); p. 711 View in Reaxys

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