Ammonia → 2-Amino-6-fluoro-4-methoxybenzonitrile

Reaction equation

[F:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[C:6](F)[C:3]=1[C:4]#[N:5].[NH3:13]>>[NH2:13][C:6]1[CH:7]=[C:8]([O:10][CH3:11])[CH:9]=[C:2]([F:1])[C:3]=1[C:4]#[N:5]

Participants

Reactant 2

HCID 222Ammonia

HCID 27787722,6-Difluoro-4-methoxybenzonitrile

Product 1

HCID 223351772-Amino-6-fluoro-4-methoxybenzonitrile

Conditions

Temperature: 140 °C

Procedure

2,6-Difluoro-4-methoxy-benzonitrile (Mol. Cryst. Liq. Cryst. 1989, 172) (200 mg, 1.18 mmol) was dissolved in ethanolic ammonia (2M solution, 10 ml) and the mixture was heated at 140° C. in an autoclave for 16 hours. The reaction mixture was cooled to room temperature and the solvent was evaporated under reduced pressure. The residue was purified by chromatography on silica gel using ethyl acetate in pentane as eluant (20:80) to give the title compound as a white solid (165 mg). LRMS: m/z (ES+) 189 [MNa+]

Workup

temperatureThe reaction mixture was cooled to room temperature
customthe solvent was evaporated under reduced pressure
customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-d498532a0f0a47ce9d470456ed8f59b9
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06936619B2

Reaction notes

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