Formic Acid → N-(2-Chloro-3-fluorophenyl)formamide

HRID 448910

Reaction equation

HRID 448910 reaction equation
C(O[C:5](=[O:7])C)(=O)C.C(O)=O.[Cl:11][C:12]1[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:13]=1[NH2:14]>>[Cl:11][C:12]1[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:13]=1[NH:14][CH:5]=[O:7]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 888842-Chloro-3-fluoroaniline

Product 1

HCID 57346568N-(2-Chloro-3-fluorophenyl)formamideYield 95.1%

Conditions

Temperature
60 °C

Procedure

A solution of acetic anhydride (10 mL, 106 mmol) and formic acid (30 mL, 795 mmol) was stirred at room temperature for 10 mins. 2-Chloro-3-fluoroaniline (2.9 g, 20 mmol) was added and the reaction mixture was stirred at 60° C. for 1.5 h. After cooling to room temperature, the solvents were removed in vacuo and the residue was redissolved in DCM (100 mL) and was washed with sat aq. NaHCO3 until the aqueous phase had a measured pH of 8. The organic layer was further washed with water (2×100 mL), separated and dried over MgSO4. Filtration and concentration in vacuo gave N-(2-chloro-3-fluoro-phenyl)-formamide (3.3 g, 95%) as a colorless solid which did not require further purification. MS (M+H)+: 173.9, tR=2.04 min (method 1).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvents were removed in vacuo
  3. dissolutionthe residue was redissolved in DCM (100 mL)
  4. washwas washed with sat aq. NaHCO3 until the aqueous phase
  5. washThe organic layer was further washed with water (2×100 mL)
  6. customseparated
  7. dry with materialdried over MgSO4
  8. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-807a0f3beb274a029b1abffe55b10786
Source dataset
uspto-grants-2013_07
Patent number
US08481738B2

Linked notes

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