Water → 5-Chloro-1H-indole-3-carboxylic acid

HRID 2187656Notes

Reaction equation

HRID 2187656 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[OH2:11].CN([CH:15]=[O:16])C>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:15]([OH:16])=[O:11]

Participants

4

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 871105-Chloroindole

Product 1

HCID 178402465-Chloro-1H-indole-3-carboxylic acid

Procedure

A solution of 5.0 g (33.0 mmol) of commercially available 5-chloro-1H-indole in 50 ml dry DMF was kept at 0° C., while 7.35 g (35.0 mmol) trifluoroacetanhydride was added dropwise. After 3 h stirring at room temperature the mixture was poured into 200 ml water, and the precipitate was filtered with suction and heated with reflux overnight in 200 ml 20% NaOH. It was extracted twice with dichloromethane, and the aqueous layer was acidified with hydrochloric acid. The crystalline title compound was collected by filtration and dried in vacuo.

Workup

  1. customwas kept at 0° C., while 7.35 g (35.0 mmol) trifluoroacetanhydride
  2. additionwas added dropwise
  3. filtrationthe precipitate was filtered with suction
  4. temperatureheated
  5. temperaturewith reflux overnight in 200 ml 20% NaOH
  6. extractionIt was extracted twice with dichloromethane
  7. filtrationThe crystalline title compound was collected by filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-25deb80635d546c8a6b3caf456602d09
Source dataset
uspto-grants-2002_06
Patent number
US06410562B1

Reaction notes

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