Hydrochloric Acid → 1-(4-chlorobenzyl)-3-methyl-1H-indole-2-carboxylic acid

HRID 83683Notes

Reaction equation

HRID 83683 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH3:16])=[C:8]2[C:17]([O:19]CC)=[O:18])=[CH:4][CH:3]=1.[OH-].[Na+].O.Cl>CCO>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH3:16])=[C:8]2[C:17]([OH:19])=[O:18])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 68380183ethyl 1-(4-chlorobenzyl)-3-methyl-1H-indole-2-carboxylate

Product 1

HCID 683797421-(4-chlorobenzyl)-3-methyl-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

ethyl 1-(4-chlorobenzyl)-3-methyl-1H-indole-2-carboxylate (480 mg, 1.46 mmol) was dissolved in EtOH (15 mL) and 10% aq. NaOH was added (6 mL). The reaction was allowed to stir at rt for 32 h, at which time as much solvent was stripped off as possible, water was added, and the mixture cooled in an ice bath. The mixture was acidified with concentrated HCl and the precipitate collected over a filter. The title compound was obtained as a white powder that was not purified or characterized further. (Yield: 430 mg, 1.435 mmol, 98%)

Workup

  1. additionwas added
  2. temperaturethe mixture cooled in an ice bath
  3. customthe precipitate collected over a filter

Sources & evidence

ORD record
ord-3b5ed9349d8747cb9ec225d9d34ca73a
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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