HCID 14064733, compound → 4-Fluoroindole-2-carboxylic acid

HRID 1051347Notes

Reaction equation

HRID 1051347 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[CH2:11][C:12](=O)[C:13]([OH:15])=[O:14]>[NH4+].[OH-].O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[CH:11]=[C:12]([C:13]([OH:15])=[O:14])[NH:8]2

Participants

4

Reactant 1

HCID 14064733HCID 14064733, compound

Product 1

HCID 40355794-Fluoroindole-2-carboxylic acidYield 22%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14923Ammonium HydroxideSolvent2×

Procedure

A solution of 32 (4.8 g, 31 mmol) in 4% NH4OH (60 mL) was added to a suspension of ferrous hydroxide that was prepared from ferrous sulfate heptahydrate (52.45 g, 188.7 mmol) and concentrated NH4OH (23 mL) in water (200 mL). The mixture was maintained at the boiling point for five minutes. The ferric hydroxide was separated by filtration and washed repeatedly with dilute NH4OH and water. The filtrate was acidified with dilute HCl. The resulting solid was collected by filtration to afford 1.2 g (22%) of 4-fluoro-1H-indole-2-carboxylic acid (34) as a white solid, which was used in the next step without further purification.

Workup

  1. temperatureThe mixture was maintained at the boiling point for five minutes
  2. customThe ferric hydroxide was separated by filtration
  3. washwashed repeatedly with dilute NH4OH and water
  4. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-5e258977df7b424ba04d3da5b9c707ca
Source dataset
uspto-grants-2016_07
Patent number
US09388171B2

Reaction notes

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