Lithium Hydroxide → 5-Chloro-6-fluoro-1H-indole-2-carboxylic acid

HRID 459460Notes

Reaction equation

HRID 459460 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][C:6]([C:12]([O:14]C)=[O:13])=[CH:5]2.[OH-].[Li+]>O1CCCC1.CO.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][C:6]([C:12]([OH:14])=[O:13])=[CH:5]2

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 18986230Methyl 5-chloro-6-fluoro-1H-indole-2-carboxylate

Product 1

HCID 189862355-Chloro-6-fluoro-1H-indole-2-carboxylic acidYield 97.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 5-chloro-6-fluoroindole-2-carboxylate (461 mg) was dissolved in a mixed solvent of tetrahydrofuran (15 ml), methanol (10 ml) and water (10 ml), lithium hydroxide (283 mg) was added at room temperature, and the mixture was stirred for 4 hours. The solvent was distilled off under reduced pressure, and 1N hydrochloric acid was added to the residue to weakly acidify it. The resultant powder was collected by filtration and dried to obtain the title compound (422 mg) as colorless powder.

Workup

  1. additionwas added at room temperature
  2. distillationThe solvent was distilled off under reduced pressure, and 1N hydrochloric acid
  3. additionwas added to the residue
  4. filtrationThe resultant powder was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-85bfa3b7691846cda1283c13446a980a
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Reaction notes

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