Lithium Hydroxide → 5-Bromo-1H-indole-7-carboxylic acid

HRID 387246Notes

Reaction equation

HRID 387246 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13]C)=[O:12])[CH:10]=1)[NH:7][CH:6]=[CH:5]2.[OH-].[Li+]>CO.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([OH:13])=[O:12])[CH:10]=1)[NH:7][CH:6]=[CH:5]2

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 24728848methyl 5-bromo-1H-indole-7-carboxylate

Product 1

HCID 533992575-Bromo-1H-indole-7-carboxylic acidYield 99.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 5-bromo-1H-indole-7-carboxylate (5 g, 19.7 mmol) was dissolved in methanol (200 mL) and a solution of lithium hydroxide (0.99 g, 41 mmol) in water (10 mL) was added. The mixture was heated at reflux for 50 hours. The methanol was removed in vacuo and the residue diluted with aqueous hydrochloric acid (2 M). The resulting precipitate was filtered off and dried in a heated vacuum pistol to give 4.7 g (99%) of the title compound as a beige solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 50 hours
  3. customThe methanol was removed in vacuo
  4. additionthe residue diluted with aqueous hydrochloric acid (2 M)
  5. filtrationThe resulting precipitate was filtered off
  6. customdried in a heated vacuum pistol

Sources & evidence

ORD record
ord-f3a48b26cb5549f4a99b5095a0f6db4c
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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