Ammonia → 1-[5-fluoro-2-(1H-1,2,4-triazol-1-yl)phenyl]methanamine

HRID 857773Notes

Reaction equation

HRID 857773 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[C:6]([CH:9]=1)[C:7]#[N:8].N>CO.[Ni]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[C:6]([CH2:7][NH2:8])[CH:9]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 218662545-fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile

Product 1

HCID 210699311-[5-fluoro-2-(1H-1,2,4-triazol-1-yl)phenyl]methanamineYield 78%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of 5-fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile (200 mg, 1.0 mmol) in methanol saturated with ammonia (30 mL) was stirred in the presence of Raney nickel (50% slurry in water, washed with methanol, catalytic amount) under a hydrogen atmosphere (balloon) for 2 days. The reaction mixture was filtered through Celite and concentrated to give the title compound as a light green foam (150 mg). 1H NMR (400 MHz, DMSO-d6): δ 8.69 (br, 2H) 7.8 (br s, 1H), 7.42 (s, 1H), 7.29 (s, 1H), 7.17 (s, 1H). 3.98 (br s, 2H)

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-dad74fbaf45d4bb79c3dcdd3a7a76aba
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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