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

HRID 1442578ノート

反応式

HRID 1442578 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-01abe0416892488892364ae521688015
出典データセット
uspto-grants-2010_02
特許番号
US07659267B2

反応ノート

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