2-(2,6-dichloro-phenyl)-1H-indole-5-carboxylic acid methyl ester → 2-(2,6-dichloro-phenyl)-1H-indole-5-carboxylic acid

HRID 1514926Notes

Reaction equation

HRID 1514926 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:21])=[CH:8]2)=[O:4]>[Li+].[OH-].C1COCC1>[Cl:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([Cl:20])[C:14]=1[C:9]1[NH:10][C:11]2[C:7]([CH:8]=1)=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:13][CH:12]=2

Participants

4

Reactant 1

HCID 669659532-(2,6-dichloro-phenyl)-1H-indole-5-carboxylic acid methyl ester

Product 1

HCID 669657142-(2,6-dichloro-phenyl)-1H-indole-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(2,6-dichloro-phenyl)-1H-indole-5-carboxylic acid methyl ester in 2N LiOH aqueous solution (1 mL) and THF (1 mL) was stirred at room temperature for 16 h. The mixture was washed with Et2O. The aqueous layer was acidified with 1N HCl aqueous solution, extracted with Et2O. The organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to give 2-(2,6-dichloro-phenyl)-1H-indole-5-carboxylic acid as a white solid: MS (m/z) 306.1 (M+1).

Workup

  1. washThe mixture was washed with Et2O
  2. extractionextracted with Et2O
  3. dry with materialThe organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3ebba98f0d4f4e34b5a27452e3ac2736
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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