Ethyl (E)-2-methyl-3-(4-nitrophenyl)prop-2-enoate → Ethyl 3-(4-aminophenyl)-2-methylpropanoate

Reaction equation

[CH3:1]/[C:2](=[CH:8]\[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1)/[C:3]([O:5][CH2:6][CH3:7])=[O:4].[H][H]>C(O)C.[Pd]>[NH2:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][CH:2]([CH3:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:14][CH:13]=1

Participants

Procedure

To a solution of (E)-ethyl 2-methyl-3-(4-nitrophenyl)acrylate (645) (2.49 g, 10.6 mmol) in ethanol (100 mL) was added Pd/C (250 mg, 10% Degussa type). A balloon of hydrogen gas was added and the reaction was evacuated and back-filled with hydrogen three times. The reaction was stirred overnight at room temperature, was filtered through a pad of celite and concentrated in vacuo to give ethyl 3-(4-aminophenyl)-2-methylpropanoate (646).