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

HRID 428021Notes

Reaction equation

HRID 428021 reaction equation
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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d5989099a3744c66bdf5bc6bb1d39ccc
Source dataset
uspto-grants-2001_11
Patent number
US06313151B1

Reaction notes

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