Formic Acid → N-(2-Acetyl-4-fluorophenyl)-N-methylformamide

HRID 358677Notes

Reaction equation

HRID 358677 reaction equation
C(OC(=O)C)(=O)C.[CH:8]([OH:10])=O.[F:11][C:12]1[CH:13]=[CH:14][C:15]([NH:21][CH3:22])=[C:16]([C:18](=[O:20])[CH3:19])[CH:17]=1.[OH-].[Na+]>O>[C:18]([C:16]1[CH:17]=[C:12]([F:11])[CH:13]=[CH:14][C:15]=1[N:21]([CH3:22])[CH:8]=[O:10])(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 450864161-(5-Fluoro-2-(methylamino)phenyl)ethanone

Product 1

HCID 86744646N-(2-Acetyl-4-fluorophenyl)-N-methylformamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of acetic anhydride (4.6 ml) and formic acid (3.1 3 ml) was stirred at 60° for 2 hours and then cooled to 10°. 5'-Fluoro-2'-(methylamino)acetophenone (3.0 g) was then added and the mixture stirred overnight. The solution was cooled in an ice-bath and water (20 ml) added followed by aqueous sodium hydroxide (specific gravity 1.5) added dropwise to pH 10. The mixture was extracted with dichloromethane (3×30 ml) and the combined extracts dried over magnesium sulphate to give a solution of 2'-acetyl-4'-fluoro-N-methylformanilide.

Workup

  1. temperaturecooled to 10°
  2. stirringthe mixture stirred overnight
  3. temperatureThe solution was cooled in an ice-bath
  4. additionadded dropwise to pH 10
  5. extractionThe mixture was extracted with dichloromethane (3×30 ml)
  6. dry with materialthe combined extracts dried over magnesium sulphate

Sources & evidence

ORD record
ord-2b5abd646a5c48d29f7ec7c02f033e1a
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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