Hydrochloric Acid → 1H-indole-6-carboxylic acid

HRID 572146Notes

Reaction equation

HRID 572146 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12]C)=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.[Li+].[OH-].Cl>CO.O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([OH:12])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 639844Methyl indole-6-carboxylate

Product 1

HCID 5952301H-indole-6-carboxylic acidYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl indole-6-carboxylate (3.0 g) in MeOH (34 mL), a 3M aqueous solution of LiOH (17 mL, 3.0 equiv.) was added. The reaction mixture was heated at reflux for 1 Hr, then cooled at 0° C., diluted with water (50 mL) and acidified with HCl 12M (5 mL). The mixture was extracted with AcOEt (3*30 mL). The combined organic layers were washed with brine (30 mL), dried over MgSO4 and concentrated to give the product as a yellow solid (2.3 g, 85%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1 Hr
  3. extractionThe mixture was extracted with AcOEt (3*30 mL)
  4. washThe combined organic layers were washed with brine (30 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7c2d05bc3a94418484715d9f46ddd78e
Source dataset
uspto-grants-2015_05
Patent number
US09029393B2

Reaction notes

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