Formic Acid → 2'-acetyl-6'-fluoro-N-methylformanilide

HRID 358672Notes

Reaction equation

HRID 358672 reaction equation
C(OC(=O)C)(=O)C.[F:8][C:9]1[C:10]([NH:18][CH3:19])=[C:11]([C:15](=[O:17])[CH3:16])[CH:12]=[CH:13][CH:14]=1.[CH:20]([OH:22])=O>>[C:15]([C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([F:8])[C:10]=1[N:18]([CH3:19])[CH:20]=[O:22])(=[O:17])[CH3:16]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 450864173'-Fluoro-2'-(methylamino)acetophenone

Product 1

HCID 231281372'-acetyl-6'-fluoro-N-methylformanilide

Procedure

A mixture of acetic anhydride (27 ml) and formic acid (18.4 ml) was stirred at 50° for 135 minutes and then cooled to ambient temperature. 3'-Fluoro-2' (methylamino)acetophenone (20.48 g) was then added and the solution stirred overnight. Excess acetic formic anhydride was removed under reduced pressure at 30° and the residue then cooled to 5°. Water (92 ml) followed by aqueous sodium hydroxide (specific gravity 1.5) were then added dropwise to pH 7 whilst maintaining the temperature below 5°. The mixture was extracted with dichloromethane (3×35 ml) and the combined extracts were washed with saturated aqueous sodium carbonate (50 ml) then aqueous sodium chloride (6M, 50 ml) and dried over magnesium sulphate to give a solution of 2'-acetyl-6'-fluoro-N-methylformanilide.

Workup

  1. stirringthe solution stirred overnight
  2. customExcess acetic formic anhydride was removed under reduced pressure at 30°
  3. temperaturethe residue then cooled to 5°
  4. additionwere then added dropwise to pH 7
  5. temperaturewhilst maintaining the temperature below 5°
  6. extractionThe mixture was extracted with dichloromethane (3×35 ml)
  7. washthe combined extracts were washed with saturated aqueous sodium carbonate (50 ml)
  8. dry with materialaqueous sodium chloride (6M, 50 ml) and dried over magnesium sulphate

Sources & evidence

ORD record
ord-07c442e101fc4ed48f71715b4fa7c98a
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

Loading…