Sodium Hydroxide → 6-Chloro-2-(4-chlorobenzoyl)indol-3-acetic acid

HRID 396576Notes

Reaction equation

HRID 396576 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][C:11]([Cl:15])=[CH:12][CH:13]=2)[NH:8][C:7]=1[C:16](=[O:24])[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)C.[OH-].[Na+]>CO.O>[Cl:15][C:11]1[CH:10]=[C:9]2[C:14]([C:6]([CH2:5][C:4]([OH:25])=[O:3])=[C:7]([C:16](=[O:24])[C:17]3[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=3)[NH:8]2)=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11057884[6-Chloro-2-(4-chloro-benzoyl)-1H-indol-3-yl]-acetic acid ethyl ester

Product 1

HCID 97983746-Chloro-2-(4-chlorobenzoyl)indol-3-acetic acidYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of [6-chloro-2-(4-chloro-benzoyl)-1H-indol-3-yl]-acetic acid ethyl ester (200 mg, 0.532 mmol) in methanol (2 ml) and water (0.8 ml) was added sodium hydroxide (137 mg, 3.43 mmol). The reaction mixture was stirred 24 hours, and was concentrated to a low volume. Water (4 ml) was added, the material was transferred to a separatory fumnel and was washed with dichloromethane (5 ml). The aqueous layer was acidified to pH 1 with 1N hydrochloric acid and was extracted with ethyl acetate (15 ml). The organic layer was dried over magnesium sulfate, filtered, and concentrate to afford [6-chloro-2-(4-chloro-benzoyl)-1H-indol-3-yl]-acetic acid (150 mg, 81%). The 1H NMR spectrum was identical with the one obtained for the compound prepared by the method described in example 2.

Workup

  1. concentrationwas concentrated to a low volume
  2. additionWater (4 ml) was added
  3. washwas washed with dichloromethane (5 ml)
  4. extractionwas extracted with ethyl acetate (15 ml)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-6d15a6f91e3c45aca1278ae4b205b26a
Source dataset
uspto-grants-2003_08
Patent number
US06608070B1

Reaction notes

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