Potassium Carbonate → Benzoic acid, 2-amino-4-cyano-, methyl ester

HRID 1442578Notes

Reaction equation

HRID 1442578 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([NH:19]C(=O)C(F)(F)F)[CH:10]=1)#[N:8]>CO>[NH2:19][C:11]1[CH:10]=[C:9]([C:7]#[N:8])[CH:18]=[CH:17][C:12]=1[C:13]([O:15][CH3:16])=[O:14]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 58610113Methyl 4-cyano-2-(2,2,2-trifluoroacetamido)benzoate

Product 1

HCID 10103677Benzoic acid, 2-amino-4-cyano-, methyl esterYield 77.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Potassium carbonate (60.3 g, 436 mmol) was added to a methanol suspension (850 mL) of methyl 4-cyano-2-[(trifluoroacetyl)amino]benzoate (108 g, 397 mmol) and the mixture was stirred at 50° C. for 2 hours. After cooling, methanol was distilled off under reduced pressure and water was added to the residue. The mixture was extracted twice with ethyl acetate. The combined organic layers were washed with 0.5M hydrochloric acid and then saturated brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was crystallized from ethyl acetate-diisopropyl ether to give the title compound (53.9 g, 76%).

Workup

  1. temperatureAfter cooling
  2. distillationmethanol was distilled off under reduced pressure and water
  3. additionwas added to the residue
  4. extractionThe mixture was extracted twice with ethyl acetate
  5. washThe combined organic layers were washed with 0.5M hydrochloric acid
  6. dry with materialsaturated brine, dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was crystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-01abe0416892488892364ae521688015
Source dataset
uspto-grants-2010_02
Patent number
US07659267B2

Reaction notes

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