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

HRID 428021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 428021
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

Komponenten

5

Edukt 2

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

Produkt 1

HCID 120695493-(4-Methoxybenzoyl)amino-2-indolecarboxylic acidAusbeute 68,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d5989099a3744c66bdf5bc6bb1d39ccc
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313151B1

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