Tetrahydrofuran → 5-Chloro-3-methyl-1H-indole-2-carboxylic acid

HRID 379009Notes

Reaction equation

HRID 379009 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([C:16]=1[CH3:17])=[CH:14][C:13]([Cl:18])=[CH:12][CH:11]=2)=[O:7])C.O1CCCC1>CO>[Cl:18][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:6]([OH:7])=[O:5])=[C:16]2[CH3:17]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 9498591H-Indole-2-carboxylic acid, 5-chloro-3-methyl-, ethyl ester

Product 1

HCID 31597065-Chloro-3-methyl-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

2N NaOH (20 mL) was added to a suspension of 5-chloro-3-methyl-1H-indole-2-carboxylic acid ethyl ester (7.0 g, 29.4 mmol) in methanol (50 mL) and the resulting mixture stirred at 25° C. for 18 hours. Tetrahydrofuran (100 mL) was added and the resulting solution heated at reflux for 30 minutes and concentrated. The residue was dissolved in water and the resulting solution extracted twice with ethyl acetate. The aqueous layer was acidified and the precipitate collected by filtration and washed with water (5.24 g).

Workup

  1. temperaturethe resulting solution heated
  2. temperatureat reflux for 30 minutes
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in water
  5. extractionthe resulting solution extracted twice with ethyl acetate
  6. filtrationthe precipitate collected by filtration
  7. washwashed with water (5.24 g)

Sources & evidence

ORD record
ord-3c7f72fa70bf480582119993d84dd1f0
Source dataset
uspto-grants-2001_10
Patent number
US06297269B1

Reaction notes

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