Hydrochloric Acid → 5-Fluoro-3-methyl-1H-indole-2-carboxylic acid

HRID 2219448Notes

Reaction equation

HRID 2219448 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13]CC)=[O:12])=[C:5]2[CH3:16].[OH-].[K+].Cl>C(O)C.O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=[O:12])=[C:5]2[CH3:16]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 930786ethyl 5-fluoro-3-methyl-1H-indole-2-carboxylate

Product 1

HCID 11329675-Fluoro-3-methyl-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl 5-fluoro-3-methyl-1H-indole-2-carboxylate (8.3 g, 37.5 mmol) and potassium hydroxide (6.3 g, 112.5 mmol) in a mixture of ethanol (20 mL) and water (15 mL) was heated at reflux for 1 hour. The volume was reduced to 10 mL under reduced pressure and the solution brought to an acidic pH with a 3N aqueous solution of hydrochloric acid. The resulting precipitate was filtered, washed with water (100 mL) and dried in vacuo at 80° C. overnight to afford 5-fluoro-3-methyl-1H-indole-2-carboxylic acid as a white solid. MS (ES) m/z 192.0.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water (100 mL)
  5. customdried in vacuo at 80° C. overnight

Sources & evidence

ORD record
ord-b6cb263215904e4194a3a6c04162d97a
Source dataset
uspto-grants-2008_08
Patent number
US07414052B2

Reaction notes

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