Ammonia → (2-(1H-IMIDAZOL-2-YL)PHENYL)METHANAMINE

HRID 857702Notes

Reaction equation

HRID 857702 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[C:8]#[N:9].N>C(O)C.[Ni]>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH2:8][NH2:9]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 114010062-(1H-imidazol-2-yl)benzonitrile

Product 1

HCID 11171256(2-(1H-IMIDAZOL-2-YL)PHENYL)METHANAMINE

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-(1H-imidazol-2-yl)-benzonitrile (50 mg, 0.30 mmol) in ethanol saturated with ammonia (5 ml) was stirred in the presence of Raney nickel (50% slurry in water, washed with ethanol, catalytic amount) under a hydrogen atmosphere for 2 h. The reaction mixture was filtered over celite and concentrated to give 2-(1H-imidazol-2-yl)-benzylamine; 1H NMR (CDCl3, 400 MHz) δ 8.13 (d, 1H, J=7.5 Hz), 7.42 (m, 1H), 7.28 (m, 2H), 7.18 (bs, 2H), 3.96 (s, 2H).

Workup

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

Sources & evidence

ORD record
ord-6ba0c3291b4a406e8bd9ec5382042fa2
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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