Lithium Hydroxide → 6-Chloro-1H-indole-5-carboxylic acid

HRID 1976779Notes

Reaction equation

HRID 1976779 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:11]([O:13]C)=[O:12].[Li+].[OH-].[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 14798Sodium HydroxideHCID 10727132Methyl 6-chloro-1H-indole-5-carboxylate

Product 1

HCID 225574516-Chloro-1H-indole-5-carboxylic acidYield 60.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of Example 58B (1.17 g, approximately 5.6 mmol) in THF (50 mL) was treated with 1M LiOH (56 mL, 56 mmol), heated at 50° C., stirred for 18 hours, treated with 1M NaOH, washed with diethyl ether, acidified with HCl, and extracted with ethyl acetate. The extract was dried (MgSO4), filtered, and concentrated. The concentrate was purified on silica gel with 50% ethyl acetate/hexanes to provide of 660 mg of the desired product.

Workup

  1. washwashed with diethyl ether
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified on silica gel with 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-83e1b6ba1eb343189e593abfa557bec4
Source dataset
uspto-grants-2001_05
Patent number
US06228868B1

Reaction notes

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