Hydrochloric Acid → 1H-Indole-3-carboxylic acid, 7-fluoro-1-methyl-

HRID 1494432Notes

Reaction equation

HRID 1494432 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH3:11])[CH:8]=[C:7]2[CH:12]=[O:13].P([O-])([O-])(O)=[O:15].[Na+].[Na+].[Mn]([O-])(=O)(=O)=O.[K+].Cl>C(O)(C)(C)C>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH3:11])[CH:8]=[C:7]2[C:12]([OH:15])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24203Sodium Phosphate, DibasicHCID 516875Potassium PermanganateHCID 221390377-Fluoro-1-methylindole-3-carboxaldehyde

Product 1

HCID 198280791H-Indole-3-carboxylic acid, 7-fluoro-1-methyl-

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

7-Fluoro-1-methylindole-3-carboxaldehyde (1.0 g) was dissolved in t-butanol (50 ml). 1.25M Sodium hydrogen phosphate (20 ml) was added followed by 1.0M potassium permanganate (30 ml), and the mixture was stirred at 20 for 16h. 2M Hydrochloric acid (200 ml) was then added and the mixture was extracted with ethyl acetate (2×200 ml). The combined, dried organic extracts were evaporated in vacuo to leave a solid which was purified by FCC eluting with hexane:ether (1:1) followed by hexane:ether:acetic acid (50:50:1) to give the title compound (192 mg), m.p. 225°-227°.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2×200 ml)
  2. customdried organic extracts were evaporated in vacuo
  3. customto leave a solid which
  4. customwas purified by FCC
  5. washeluting with hexane:ether (1:1)

Sources & evidence

ORD record
ord-88868a75be4f4bfc8ed32b7a7fc444bf
Source dataset
uspto-grants-1991_06
Patent number
US05026722

Reaction notes

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