Sodium Hydroxide → 3-(4-Methoxybenzoyl)amino-2-indolecarboxylic acid

HRID 1355628ノート

反応式

HRID 1355628 の反応式
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[NH:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])C.[OH-].[Na+]>O1CCCC1.O>[CH3:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([C:16]([NH:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[C:4]([OH:5])=[O:3])=[O:25])=[CH:22][CH:21]=1

参加物

5

反応物 2

HCID 14798Sodium Hydroxide2 回HCID 751363Ethyl 3-(4-methoxybenzamido)-1H-indole-2-carboxylate

生成物 1

HCID 120695493-(4-Methoxybenzoyl)amino-2-indolecarboxylic acid収率 68.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 3-(4-methoxybenzoyl)amino-2-indolecarboxylic acid ethyl ester (720 mg, 2.13 mmol) in tetrahydrofuran (7 mL) was added 5 N aqueous sodium hydroxide (2 mL). The resulting mixture was stirred for 10 h at room temperature. An additional portion of 5 N aqueous sodium hydroxide (5 mL) was added and the mixture heated at 60° C. for 5 h. The mixture was cooled to room temperature, stirred for 10 h, diluted with water, and extracted with diethyl ether. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with three fresh portions of ethyl acetate. The combined ethyl acetate fractions were dried (sodium sulfate), filtered, and concentrated in vacuo to provide 450 mg (68%) of the title compound as a yellow solid.

後処理

  1. temperaturethe mixture heated at 60° C. for 5 h
  2. temperatureThe mixture was cooled to room temperature
  3. stirringstirred for 10 h
  4. extractionextracted with diethyl ether
  5. extractionextracted with three fresh portions of ethyl acetate
  6. dry with materialThe combined ethyl acetate fractions were dried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-fea0cbb9723f4ec08106a02083e65358
出典データセット
uspto-grants-2003_07
特許番号
US06586459B2

反応ノート

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