Ethyl-m-nitrocinnamate → Ethyl 3-(3-Aminophenyl)propionate

HRID 1256081Notes

Reaction equation

HRID 1256081 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 94827Ethyl-m-nitrocinnamate

Product 1

HCID 82314Ethyl 3-(3-Aminophenyl)propionateYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of ethyl 3-(3-nitrophenyl)acrylate (63 g, 284 mmol) and Pd/C (6.3 g) in MeOH (800 ml) were stirred under 40 psi of H2 at room temperature for 2 hr, then filtered through celite to give the product ethyl 3-(3-aminophenyl)propanoate (48 g, yield 89%). 1H NMR MeOD 400 MHz. δ 7.00-6.51 (m, 4H), 4.10-4.04 (m, 2H), 2.79-2.76 (m, 2H), 2.56-2.52 (m, 2H), 1.20-1.17 (m, 3H).

Workup

  1. filtrationfiltered through celite

Sources & evidence

ORD record
ord-c4732fd087dc4a45b9215f408f0607c4
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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