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

HRID 1355628노트

반응식

HRID 1355628 반응식
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

참가 물질

5

반응물 2

HCID 14798Sodium Hydroxide2회HCID 751363Ethyl 3-(4-methoxybenzamido)-1H-indole-2-carboxylate

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fea0cbb9723f4ec08106a02083e65358
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586459B2

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