Hydrochloric Acid → 5-Bromo-1H-indole-7-carboxylic acid

HRID 855181Notes

Reaction equation

HRID 855181 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([Br:14])[CH:8]=[C:9]2[C:13]=1[NH:12][CH:11]=[CH:10]2)=[O:4].Cl>[OH-].[Na+].C(O)C>[Br:14][C:7]1[CH:8]=[C:9]2[C:13](=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=1)[NH:12][CH:11]=[CH:10]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 24728848methyl 5-bromo-1H-indole-7-carboxylate

Product 1

HCID 533992575-Bromo-1H-indole-7-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
40 °C

Procedure

409 mg of 5-bromo-1H-indole-7-carboxylic acid methyl ester (1.61 mmol) were suspended in a mixture of 1.6 ml 2N NaOH and 1.6 ml ethanol and stirred at 40° C. for 2 h. After cooling down, the mixture was treated with 2N aqueous HCl, and extracted twice with EtOAc. The organic phase was the washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo, leading to 353 mg of 5-bromo-1H-indole-7-carboxylic acid as a light brown solid (85%). MS (ISP) 237.9 (M−H)−.

Workup

  1. temperatureAfter cooling down
  2. extractionextracted twice with EtOAc
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4e2f62583114470e8c88e093fe7f8b69
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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