Pyridine → 4-Fluoro-N-methoxy-N-methylbenzamide

HRID 52179Notes

Reaction equation

HRID 52179 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.Cl.[CH3:12][NH:13][O:14][CH3:15].N1C=CC=CC=1>C(Cl)Cl>[CH3:15][O:14][N:13]([CH3:12])[C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 678794-Fluorobenzoyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 140693474-Fluoro-N-methoxy-N-methylbenzamideYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0° C. solution of 4-fluorobenzoyl chloride (11.9 g, 75.0 mmol) in CH2Cl2 (150 mL) was added N,O-dimethylhydroxylamine hydrochloride (8.00 g, 82.0 mmol) and a solution of pyridine (13.0 g, 164 mmol) in CH2Cl2 (25 mL). The cold bath was removed and the reaction mixture was stirred for 2 hours at ambient temperature and then was washed with 0.5N aqueous HCl (3×100 mL), saturated aqueous NaHCO3, and brine. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give N-methoxy-N-methyl-4-fluorobenzamide (13.3 g, 97% ) as an oil.

Workup

  1. customThe cold bath was removed
  2. washwas washed with 0.5N aqueous HCl (3×100 mL), saturated aqueous NaHCO3, and brine
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3aadff4dcc05462ea3a7e32085325492
Source dataset
uspto-grants-1997_04
Patent number
US05616596

Reaction notes

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