Formic Acid → HCID 23128111, compound

HRID 358704Notes

Reaction equation

HRID 358704 reaction equation
C(OC(=O)C)(=O)C.[CH:8]([OH:10])=O.[Cl: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]([Cl: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 10655069HCID 10655069, compound

Product 1

HCID 23128111HCID 23128111, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of acetic anhydride (12 ml) and formic acid (8 ml) was heated at 55° for 3 hours and then cooled to ambient temperature. 4'-Chloro-2'-(methylamino)acetophenone (9.7 g) was then added and the mixture stirred at ambient temperature overnight. Water (40 ml) was added and the mixture stirred in an ice/salt bath and neutralised by adding aqueous sodium hydroxide (specific gravity 1.5, 22 ml) whilst maintaining the temperature below 30°. The reaction 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'-chloro-N-methylformanilide.

Workup

  1. temperaturewas heated at 55° for 3 hours
  2. stirringthe mixture stirred in an ice/salt bath
  3. temperaturewhilst maintaining the temperature below 30°
  4. extractionThe reaction mixture was extracted with dichloromethane (3×50 ml)
  5. dry with materialthe combined extracts were dried over magnesium sulphate

Sources & evidence

ORD record
ord-d58b1dfe9ac14269a5958ee8dbf8a6b0
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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