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

HRID 397508Notes

Reaction equation

HRID 397508 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) δ7.69 (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-2aa9e5fb7eb04ee6b723569d4be364e3
Source dataset
uspto-grants-2003_08
Patent number
US06610701B2

Reaction notes

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