Ammonia → 1-[2-(1H-imidazol-1-yl)phenyl]methanamine

HRID 857707Notes

Reaction equation

HRID 857707 reaction equation
[N:1]1([C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[C:8]#[N:9])[CH:5]=[CH:4][N:3]=[CH:2]1.N>C(O)C.[Ni]>[N:1]1([C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[CH2:8][NH2:9])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 1902752-(1H-imidazol-1-yl)benzonitrile

Product 1

HCID 31616711-[2-(1H-imidazol-1-yl)phenyl]methanamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-imidazol-1-yl-benzonitrile (200 mg, 1.2 mmol) in ethanol saturated with ammonia (20 ml) was stirred in the presence of Raney nickel (50% slurry in water, washed with ethanol, catalytic amount) under a hydrogen atmosphere for 4 h. The reaction mixture was filtered over celite and concentrated to give 2-Imidazol-1-yl-benzylamine; 1H NMR (CDCl3, 400 MHz) δ 7.69 (bs, 1H), 7.57 (m, 1H), 7.47 (m, 1H), 7.38 (m, 1H), 7.27 (m, 1H), 7.22 (bs, 1H), 7.16 (m, 1H), 3.73 (s, 2H).

Workup

  1. filtrationThe reaction mixture was filtered over celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-0ccad98394a4462a9c1c1239db4a5a27
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

Loading…