Hydrochloric Acid → 2-(2,6-dichlorophenyl)-1H-indole-6-carboxylic acid

HRID 1514936Notes

Reaction equation

HRID 1514936 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([C:18]([O:20]C)=[O:19])[CH:12]=2.[OH-].[Na+].Cl>C(O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([C:18]([OH:20])=[O:19])[CH:12]=2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66965661methyl 2-(2,6-dichlorophenyl)-1H-indole-6-carboxylate

Product 1

HCID 669660532-(2,6-dichlorophenyl)-1H-indole-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 2-(2,6-dichlorophenyl)-1H-indole-6-carboxylate (160 mg, 500 μmol) and 1N NaOH (1.5 mL) in ethanol (25 mL) was heated at 80° C. for 18 h. The solution was cooled to ambient temperature, diluted with ethyl acetate, acidified with conc. HCl, and the layers separated. The aqueous phase was re-extracted with ethyl acetate, and the combined organic layers were dried, filtered, and the solvent was removed under reduced pressure to afford 2-(2,6-dichlorophenyl)-1H-indole-6-carboxylic acid. MS (m/z) 304.0 (M−1).

Workup

  1. temperatureThe solution was cooled to ambient temperature
  2. customthe layers separated
  3. extractionThe aqueous phase was re-extracted with ethyl acetate
  4. customthe combined organic layers were dried
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c2fc94f779ca4556a4d827901b7d9e77
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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