Potassium Hydroxide → 4-fluoro-1H-indole-7-carboxylic Acid

HRID 992352Notes

Reaction equation

HRID 992352 reaction equation
[OH-:1].[K+].[F:3][C:4]1[CH:12]=[CH:11][C:10]([C:13]#N)=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2.[OH2:15].CCO>>[F:3][C:4]1[CH:12]=[CH:11][C:10]([C:13]([OH:15])=[O:1])=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2

Participants

4

Reactant 3

HCID 14797Potassium HydroxideHCID 19096565Water ethanolHCID 224730224-Fluoro-1H-indole-7-carbonitrile

Product 1

HCID 115792174-fluoro-1H-indole-7-carboxylic Acid

Procedure

To a solution of KOH (13.04 g, 0.232 mol) in 14% H2O/EtOH (50 ml) was added 4-fluoro-7-cyanoindole (900 mg, 5.60 mmol). The resulting mixture was refluxed for 12 hours, slowly cooled to room temperature, and concentrated in vacuo to about 30 ml. The residue was acidified to pH 2 with HCl (˜5.5 N aq.). The precipitate was filtered, washed with excess of water, and dried under high vacuum to afford 4-fluoro-7-carboxyindole as a white solid (100% conversion). The material was used without further purification.

Workup

  1. temperatureThe resulting mixture was refluxed for 12 hours
  2. concentrationconcentrated in vacuo to about 30 ml
  3. filtrationThe precipitate was filtered
  4. washwashed with excess of water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-b615c55141fc4dc18d7dc8427c8707f7
Source dataset
uspto-grants-2002_10
Patent number
US06469006B1

Reaction notes

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