N-Decyl-3-phenyl-3-(3-nitrophenyl)propenamide → N-Decyl-3-phenyl-3-(3-aminophenyl)propenamide

HRID 66623Notes

Reaction equation

HRID 66623 reaction equation
[CH2:1]([NH:11][C:12](=[O:30])[CH:13]=[C:14]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]>C(O)(=O)C.[Fe]>[CH2:1]([NH:11][C:12](=[O:30])[CH:13]=[C:14]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 1

HCID 53913879N-Decyl-3-phenyl-3-(3-nitrophenyl)propenamide

Product 1

HCID 53953766N-Decyl-3-phenyl-3-(3-aminophenyl)propenamide

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

Reduction of 10.7 g. of N-decyl-3-phenyl-3-(3-nitrophenyl)propenamide with 7.3 g. of iron powder in acetic acid, according to the procedure of Preparation 25, afforded the title compound as an oil. This product was chromatographed on 370 g. of silica gel, eluting with chloroform containing 1% ethanol. This gave 2.2 g. of trans-N-decyl-3-phenyl-3-(3-aminophenyl)propenamide and 0.7 g of cis-N-decyl-3-phenyl-3-(3-aminophenyl)propenamide. The NMR spectrum of the trans-isomer (in CDCl3) showed absorptions at 0.95 (m), 1.25 (s), 3.10 (m), 3.75 (b), 6.35 (s), 6.65 (m) and 7.30 (s) ppm. The NMR spectrum of the cis-isomer (in CDCl3) showed absorptions at 0.90 (m), 1.25 (s), 3.05 (b), 3.65 (b), 5.20 (b), 6.35 (s), 6.65 (m) and 7.15 (m) ppm.

Sources & evidence

ORD record
ord-86622ee538774dbd9a6f49712bdc860b
Source dataset
uspto-grants-1982_08
Patent number
US04342781

Reaction notes

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