Formic Acid → 2'-acetyl-5'-fluoro-N-methylformanilide

HRID 358663Notes

Reaction equation

HRID 358663 reaction equation
C(OC(=O)C)(=O)C.[CH:8]([OH:10])=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:20])[CH3:19])=[C:14]([NH:21][CH3:22])[CH:13]=1.[OH-].[Na+]>O>[C:18]([C:15]1[CH:16]=[CH:17][C:12]([F:11])=[CH:13][C:14]=1[N:21]([CH3:22])[CH:8]=[O:10])(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 199784601-[4-Fluoro-2-(methylamino)phenyl]ethanone

Product 1

HCID 231281532'-acetyl-5'-fluoro-N-methylformanilide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of acetic anhydride (26.5 ml) and formic acid (98%, 17.4 ml) was stirred at 50°-60° for 110 minutes and then cooled to ambient temperature. 4'-Fluoro-2'-(methylamino)acetophenone (19.9 g) was added and the mixture stirred overnight at ambient temperature. Water (90 ml) was added and the mixture stirred in an ice/ salt bath. Aqueous sodium hydroxide (specific gravity 1.5, 50 ml) was added dropwise over a period of 30 minutes whilst maintaining the temperature below 30°. The mixture was extracted with dichloromethane (3×50 ml) and the combined extracts were dried over magnesium sulphate to give a solution of 2'-acetyl-5'-fluoro-N-methylformanilide.

Workup

  1. stirringthe mixture stirred overnight at ambient temperature
  2. stirringthe mixture stirred in an ice/ salt bath
  3. temperaturewhilst maintaining the temperature below 30°
  4. extractionThe mixture was extracted with dichloromethane (3×50 ml)
  5. dry with materialthe combined extracts were dried over magnesium sulphate

Sources & evidence

ORD record
ord-8901c54b5f834788b3637b41773d9f7d
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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