Sodium Hydroxide → 4-chloro-5-fluoro-1H-indole-2-carboxylic acid

HRID 2396828Notes

Reaction equation

HRID 2396828 reaction equation
[Cl:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([O:14]CC)=[O:13])[NH:6]2.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([OH:14])=[O:13])[NH:6]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18986263ethyl 4-chloro-5-fluoro-1H-indole-2-carboxylate

Product 1

HCID 217108184-chloro-5-fluoro-1H-indole-2-carboxylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 6.3 g of ethyl 4-chloro-5-fluoroindole-2-carboxylate in 260 ml of ethanol was treated with 130 ml of 2N sodium hydroxide solution and stirred for 3 hours. Ethanol was evaporated and the reaction solution was adjusted to pH 1 with 25% hydrochloric acid. The precipitate was washed with water and dried. There were obtained 5.3 g (96%) of crude 4-chloro-5-fluoroindole-2-carboxylic acid which was used in the next step without further purification.

Workup

  1. customEthanol was evaporated
  2. washThe precipitate was washed with water
  3. customdried

Sources & evidence

ORD record
ord-d283c6622c654ea6adb4b2b0adeb5ba9
Source dataset
uspto-grants-1996_02
Patent number
US05494928

Reaction notes

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