Hydrochloric Acid → 5-Bromo-1-methyl-1H-indole-3-carboxylic acid

HRID 1748481Notes

Reaction equation

HRID 1748481 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Br:17])[CH:15]=2)[N:10]([CH3:18])[CH:9]=1)=[O:7])C.O.Cl>C(O)C>[Br:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH3:18])[CH:9]=[C:8]2[C:6]([OH:7])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86692444HCID 86692444, compound

Product 1

HCID 110324135-Bromo-1-methyl-1H-indole-3-carboxylic acidYield 97.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

1N Aqueous solution of sodium hydroxide (10 ml) was added at room temperature to a solution of 5-bromo-1-methyl-1H-indole-3-carboxylic acid ethyl ester (605 mg) in ethanol (10 ml) and stirred at 70° C. for three hours. After completion of the reaction, the reaction solution was cooled to room temperature, water and 1N hydrochloric acid aqueous solution were added and the precipitated solid was collected by filtration to give the titled compound (530 mg) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. temperaturethe reaction solution was cooled to room temperature
  3. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-139b6a20b53d429fbb7b8977b8edbf95
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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