Ammonium formate → 3-(2-Oxo-2-pyrrolidin-1-ylethyl)aniline

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O.C([O-])=O.[NH4+]>CO.[Pd]>[O:12]=[C:11]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[NH2:1]

Participants

Procedure

To a solution of 2.12 g of 1-[(3-nitrophenyl)acetyl]pyrrolidine obtained in stage a) below in 50 mL of methanol are added, under argon, 4.56 g of ammonium formate and 96 mg of 10% palladium-on-charcoal. The reaction mixture is stirred at room temperature for 1 hour and then filtered through Celite and concentrated under reduced pressure. The residue is taken up in water and extracted with dichloromethane. The organic phase is then washed with water and with saturated sodium chloride solution, dried over magnesium sulphate, filtered and concentrated under reduced pressure to give 1.46 g of 3-(2-oxo-2-pyrrolidin-1-ylethyl)aniline, the characteristics of which are as follows: