Methanol → 3,5-Difluoro-4-(4-methoxy-benzylamino)-benzoic acid

HRID 912165ノート

反応式

HRID 912165 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:20])[C:9]=1[NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[C:5]#N.[OH-:21].[Na+].C[OH:24]>>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:20])[C:9]=1[NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[C:5]([OH:24])=[O:21]

参加物

4

反応物 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 592447423,5-Difluoro-4-(4-methoxy-benzylamino)-benzonitrile

生成物 1

HCID 592447773,5-Difluoro-4-(4-methoxy-benzylamino)-benzoic acid

実験手順

To 3,5-difluoro-4-(4-methoxy-benzylamino)-benzonitrile (26.2 g, 95.5 mmol) obtained in Step A, methanol (300 ml) and 5M-NaOH aqueous solution (150 ml) were added, followed by heating to reflux for 58 hours. The solvent was distilled off under reduced pressure, and dichloromethane (200 ml) was added, followed by extraction with 1M-NaOH aqueous solution (200 ml×3). To the aqueous layer, 6M−HCl aqueous solution was added to adjust the pH to 6, followed by extraction with ethyl acetate (300 ml×2). After the organic layer was dried over sodium sulfate, the solvent was distilled off under reduced pressure. The resulting solid was washed with n-hexane, and the desired compound was obtained as a colorless solid (25.6 g, 91%).

後処理

  1. temperatureby heating
  2. temperatureto reflux for 58 hours
  3. distillationThe solvent was distilled off under reduced pressure, and dichloromethane (200 ml)
  4. additionwas added
  5. extractionfollowed by extraction with 1M-NaOH aqueous solution (200 ml×3)
  6. additionTo the aqueous layer, 6M−HCl aqueous solution was added
  7. extractionfollowed by extraction with ethyl acetate (300 ml×2)
  8. dry with materialAfter the organic layer was dried over sodium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. washThe resulting solid was washed with n-hexane

出典と根拠

ORDレコード
ord-77870b88f18a43e5b087a67f2f00e6d5
出典データセット
uspto-grants-2011_09
特許番号
US08022205B2

反応ノート

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