Formic Acid → n-(3-chlorophenyl)formamide

HRID 412924Notes

Reaction equation

HRID 412924 reaction equation
C(O[C:5](=[O:7])C)(=O)C.C(O)=O.[Cl:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH2:15]>>[Cl:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH:15][CH:5]=[O:7]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 79323-Chloroaniline

Product 1

HCID 232523n-(3-chlorophenyl)formamideYield 74%

Conditions

Temperature
60 °C

Procedure

Acetic anhydride (189 ml, 2.0 mol) was mixed with formic acid (91 ml, 2.4 mol) at 0° C. and the mixture was stirred at 60° C. for 1 h and then cooled to 0° C. To the solution was added dropwise 3-chloroaniline (105.7 ml, 1.0 mol) and the mixture was stirred at room temperature for 18 h. After removal of solvent in vacuo, the residue was extracted with EtOAc-H2O. The organic layer was washed with 5% aqueous citric acid, saturated aqueous NaHCO3 and brine, dried over Na2SO4 and then concentrated. The residue was crystallized from iPr2O to give the title compound (115 g, 0.739 mol, 74%) as a colorless solid.

Workup

  1. temperaturecooled to 0° C
  2. stirringthe mixture was stirred at room temperature for 18 h
  3. customAfter removal of solvent in vacuo
  4. extractionthe residue was extracted with EtOAc-H2O
  5. washThe organic layer was washed with 5% aqueous citric acid, saturated aqueous NaHCO3 and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was crystallized from iPr2O

Sources & evidence

ORD record
ord-9f8e65d62bcd42fc950bd3462e82b505
Source dataset
uspto-grants-2003_05
Patent number
US06562978B1

Reaction notes

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