Ethyl Acetate → 3-chloro-1H-indole-5-carboxylic acid

HRID 1976783Notes

Reaction equation

HRID 1976783 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13]C)=[O:12])[CH:9]=2)[NH:4][CH:3]=1.C(OCC)(=O)C>C1COCC1.[Li+].[OH-]>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([OH:13])=[O:12])[CH:9]=2)[NH:4][CH:3]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 219987283-Chloro-1H-indole-5-carboxylic acid methyl ester

Product 1

HCID 219987233-chloro-1H-indole-5-carboxylic acidYield 79.9%

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 62A (361 mg, 1.62 mmol) in THF (7 mL) and 1M LiOH (3.3 mL) was heated at 50° C. for 5 hours, treated with ethyl acetate and extracted with 10% NaHCO3 (3×). The extract was treated with 6M HCl and extracted with ethyl acetate (2×40 mL). The organic layer was dried (MgSO4), filtered, and concentrated to provide 253.2 mg of the desired compound.

Workup

  1. extractionextracted with 10% NaHCO3 (3×)
  2. additionThe extract was treated with 6M HCl
  3. extractionextracted with ethyl acetate (2×40 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c8bdc2fb37d14c0f980e8147589672c0
Source dataset
uspto-grants-2001_05
Patent number
US06228868B1

Reaction notes

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