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

HRID 2267479Notes

Reaction equation

HRID 2267479 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 the title compound as a beige solid (4.7 g).

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-d9159f617b3a44fb87ae628fc6576ec4
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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