Methanol → 4-Bromo-1H-indole-6-carboxylic acid

HRID 1443822Notes

Reaction equation

HRID 1443822 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[CH:12][NH:13]2)=[C:9]([Br:16])[CH:8]=1)=[O:6].CO>O>[Br:16][C:9]1[CH:8]=[C:7]([C:5]([OH:6])=[O:4])[CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 24728007Methyl 4-bromo-1H-indole-6-carboxylate

Product 1

HCID 247286084-Bromo-1H-indole-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (14.08 g, 352.1 mmol) in water (100 mL) was added a to a solution of 4-bromo-1H-indole-6-carboxylic acid methyl ester in methanol (14.91 mL, 58.7 mmol) at room temperature and stirred for 2.5 hours. The reaction mixture was concentrated in vacuo, 1N HCl was added, and the product was extracted with ethyl acetate to give 13.0 g of 4-bromo-1H-indole-6-carboxylic acid, which was used in the next step with no further purification. 1H NMR (400 MHz, CD3OD) δ 8.13 (t, J=1.0 Hz, 1H), 7.87 (d, J=1.3 Hz, 1H), 7.53 (t, J=3.4 Hz, 1H), 8.13 (d, J=4.2 Hz, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo, 1N HCl
  2. additionwas added
  3. extractionthe product was extracted with ethyl acetate

Sources & evidence

ORD record
ord-a653a240dae847338270c7b787995551
Source dataset
uspto-grants-2010_02
Patent number
US07662824B2

Reaction notes

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