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

HRID 627528Notes

Reaction equation

HRID 627528 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].N1C=CC=CC=1.[F:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1>C(Cl)Cl>[F:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([N:3]([O:4][CH3:5])[CH3:2])=[O:18])=[CH:15][CH:14]=1

Participants

5

Reactant 3

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

Product 1

HCID 140693474-Fluoro-N-methoxy-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To N,O-dimethylhydroxylamine hydrochloride (27.7 g, 284 mmol) in DCM (660 mL) was added pyridine (45.8 mL, 569 mmol) followed by 4-fluorobenzoyl chloride (31.0 mL, 258 mmol). The resulting suspension was stirred at room temperature for 20 hours, then was filtered to remove a white solid precipitate. The solid was washed with DCM and the filtrate was washed with 1 N aqueous HCl (2×), then water. The organic phase was dried (Na2SO4), filtered, and concentrated, yielding the crude title compound which was used without further purification.

Workup

  1. filtrationwas filtered
  2. customto remove a white solid precipitate
  3. washThe solid was washed with DCM
  4. washthe filtrate was washed with 1 N aqueous HCl (2×)
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-55b6165f0387454599bce2250a562950
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

Loading…