3-Methyl-1H-indole-5-carbonitrile → (3-methyl-1H-indol-5-yl)methanamine

Reaction equation

[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=2)[NH:4][CH:3]=1>[Ni].N.CO>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:11][NH2:12])[CH:9]=2)[NH:4][CH:3]=1

Participants

Procedure

Raney Nickel (wet, 1.0 g) was added to a stirred solution of 192 (220.0 mg, 1.41 mmol) in 2.0 M ammonia in MeOH (10 mL). The reaction mixture was hydrogenated under an H2 balloon at 1 atmospheric pressure at RT for 3 d. The reaction mixture was filtered through a pad of Celite® and the pad was rinsed well with MeOH and water. Volatile solvent from the filtrate was removed in vacuo. The aqueous phase from filtrate was thrice extracted with EtOAc. The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. Crystallization from DCM/heptane afforded 219.1 mg (97%) of (3-methyl-1H-indol-5-yl)methanamine (194) as a white solid: 1H NMR (400 MHz, CDCl3): δ 7.87 (br s, 1H), 7.49 (s, 1H), 7.29 (d, J=8.3 Hz, 1H), 7.12 (d, J=8.3 Hz, 1H), 6.95 (s, 1H), 3.95 (s, 2H), 2.31 (s, 3H), 1.59 (br s, 2H).