N-(1-Methyldecyl)-3-phenyl-3-(4-nitrophenyl)propenamide → N-(1-Methyldecyl)-3-phenyl-3-(4-aminophenyl)propenamide

HRID 66624Notes

Reaction equation

HRID 66624 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][C:19]([N+:22]([O-])=O)=[CH:18][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][C:19]([NH2:22])=[CH:18][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 53836625N-(1-Methyldecyl)-3-phenyl-3-(4-nitrophenyl)propenamide

Product 1

HCID 54412653N-(1-Methyldecyl)-3-phenyl-3-(4-aminophenyl)propenamide

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

Reduction of 6.4 g. of N-(1-methyldecyl)-3-phenyl-3-(4-nitrophenyl)propenamide with 4.2 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 220 g. of silica gel, eluting with 1:1 ethyl acetate-hexane containing 2% triethylamine. This gave 2.0 g. of trans-N-(1-methyldecyl)-3-phenyl-3-(4-aminophenyl)propenamide and 2.5 g. of cis-N-(1-methyldecyl)-3-phenyl-3-(4-aminophenyl)propenamide. The NMR spectrum of the trans-isomer (in CDCl3) showed absorptions at 0.90 (m), 1.20 (s), 3.80 (b), 5.15 (b), 6.30 (s), 6.85 (m) and 7.30 (s) ppm.

Sources & evidence

ORD record
ord-b53bc88e0e1e4c8f8b0e237eb327b506
Source dataset
uspto-grants-1982_08
Patent number
US04342781

Reaction notes

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