2-(4-Nitrophenyl)indolizine → 2-(4-Aminophenyl)indolizine

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]3[N:17]([CH:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13]3)=[CH:6][CH:5]=1)([O-])=O.[BH4-].[Na+]>CCO.CC([O-])=O.CC([O-])=O.[Cu+2]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[C:12]3[N:17]([CH:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13]3)=[CH:8][CH:9]=1

Participants

Procedure

To a suspension of 2-(4-nitrophenyl)indolizine (0.2 g, 0.84 mmol) and Cu(OAc)2 (0.16 g, 0.88 mmol) in EtOH (50 mL) was added NaBH4 (0.64 g, 16.8 mmol). The resulting mixture was stirred at room temperature for 3 hrs and concentrated in vacuo. The residue was dissolved in H2O (20 mL) and extracted with EtOAc (3×20 mL). The combined organic layers were dried (MgSO4), filtered. The filtrate was concentrated in vacuo to give a solid (0.092 g, 53%). 1H NMR (CDCl3, 400 MHz) δ: 7.87 (dd, J=6.8, 1.2 Hz, 1H), 7.44-7.95 (m, 3H), 7.31 (d, J=8.4 Hz, 1H), 6.73 (d, J=8.4 Hz, 2H), 6.59-6.64 (m, 2H), 6.42 (td, J=6.8, 1.2 Hz, 1H), 3.67 (br s, 2H). MS: m/z=209 (M+H+).