3-(5-Methyl-2-nitro-phenylamino)-hexanoic acid ethyl ester → 3-(2-Amino-5-methyl-phenylamino)-hexanoic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]([NH:10][C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=1[N+:18]([O-])=O)[CH2:7][CH2:8][CH3:9])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]([NH:10][C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=1[NH2:18])[CH2:7][CH2:8][CH3:9])[CH3:2]Participants
4
Procedure
To a solution of 3-(5-Methyl-2-nitro-phenylamino)-hexanoic acid ethyl ester (1.4 g, 4.8 mmol) in MeOH (10 mL) was added a slurry of Pd/C (wet) (0.25 g) in MeOH. The reaction mixture was saturated with H2 balloon and stirred at room temperature for 2 h. When the reaction was complete, the reaction mixture was filtered through a pad of celite. The filtrate was concentrated to afford 1.4 g of the desired product as dark purplish oil. This product was used for the next reaction without further purification.