N-[(2-Fluoro-6-methoxyphenyl)methylidene]hydroxylamine → 2-Fluoro-6-methoxybenzonitrile

HRID 1358280Notes

Reaction equation

HRID 1358280 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:3]=1[CH:4]=[N:5]O>CC(OC(C)=O)=O>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:3]=1[C:4]#[N:5]

Participants

3

Reactant 1

HCID 71350152N-[(2-Fluoro-6-methoxyphenyl)methylidene]hydroxylamine

Product 1

HCID 5231012-Fluoro-6-methoxybenzonitrileYield 100%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 2-fluoro-6-methoxybenzaldoxime (714 mg, 4.2 mmol) in Ac2O (3.6 mL) is heated at reflux for 4 hr. The reaction is cooled to r.t. and the volatiles are stripped off to give a beige solid, which is dried at 50° C. in a vacuum oven to give 2-fluoro-6-methoxybenzonitrile (635 mg, 84%). 1H NMR (DMSO) δ7.8-7.7 (1H, m), 7.14-7.07 (2H, m),3.95 (3H, s).

Workup

  1. temperatureat reflux for 4 hr
  2. customto give a beige solid, which
  3. customis dried at 50° C. in a vacuum oven

Sources & evidence

ORD record
ord-092b752e2ee645ba9fa9444bc8bc9b8d
Source dataset
uspto-grants-2003_07
Patent number
US06596726B1

Reaction notes

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