N-(1-Methyldecyl)-3-phenyl-3-(3-nitrophenyl)propenamide → N-(1-Methyldecyl)-3-phenyl-3-(3-aminophenyl)propenamide

HRID 66625Notes

Reaction equation

HRID 66625 reaction equation
[CH3:1][CH:2]([NH:12][C:13](=[O:31])[CH:14]=[C:15]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[CH:17]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]>C(O)(=O)C.[Fe]>[CH3:1][CH:2]([NH:12][C:13](=[O:31])[CH:14]=[C:15]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 1

HCID 53762315N-(1-Methyldecyl)-3-phenyl-3-(3-nitrophenyl)propenamide

Product 1

HCID 54057448N-(1-Methyldecyl)-3-phenyl-3-(3-aminophenyl)propenamide

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

Reduction of 11.6 g. of N-(1-methyldecyl)-3-phenyl-3-(3-nitrophenyl)propenamide with 7.7 g. of iron powder in glacial acetic acid, according to the procedure of Preparation 25, afforded the title compound as an oil. This product was chromatographed on 350 g. of silica gel, eluting with chloroform containing 1% ethanol. This gave 2.3 g. of trans-N-(1-methyldecyl)-3-phenyl-3-(3-aminophenyl)propenamide, 0.25 g. of cis-N-(1-methyldecyl)-3-phenyl-3-(3-aminophenyl)propenamide and 6.2 g. of a mixture of these two isomers. Rechromatography of the mixture afforded a further 0.6 g. of the cis-isomer. The NMR spectrum of the trans-isomer (in CDCl3) showed absorptions at 0.85 (m), 1.25 (s), 3.60 (b), 5.15 (b), 6.35 (s), 6.65 (m) and 7.30 (s) ppm.

Sources & evidence

ORD record
ord-35d522ef638b4eb08f007fab083e83a3
Source dataset
uspto-grants-1982_08
Patent number
US04342781

Reaction notes

Loading…