1-Methyl-1H-Indole-4-Carboxylic Acid → 1-(1-Methyl-1H-indol-4-yl)ethanone

HRID 2073524Notes

Reaction equation

HRID 2073524 reaction equation
[CH3:1][Li].[CH3:3][N:4]1[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([C:13]([OH:15])=O)[C:7]=2[CH:6]=[CH:5]1>C1COCC1>[CH3:3][N:4]1[C:12]2[C:7](=[C:8]([C:13](=[O:15])[CH3:1])[CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5]1

Participants

4

Reactant 2

HCID 149872871-Methyl-1H-Indole-4-Carboxylic AcidHCID 178418348HCID 178418348, compound

Product 1

HCID 149872881-(1-Methyl-1H-indol-4-yl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl lithium (1.59M solution in ether; 13.8 ml) was added dropwise to a stirred cold (-65° to -55°) solution of 1-methyl-1H-indole-4-carboxylic acid (1.75 g) in dry THF (50 ml) under nitrogen and stirring was continued while the mixture warmed to 0° over 2 h. The reaction was then quenched with saturated ammonium chloride solution (50 ml) and the layers were separated. The aqueous layer was further extracted with dichloromethane (2×50 ml) and the combined organic layers were washed with brine (2×50 ml), dried and evaporated in vacuo. The residual solid (1.8 g) was purified by FCC eluting with dichloromethane to give the title compound (1.6 g), m.p. 63°-64°.

Workup

  1. temperaturewarmed to 0° over 2 h
  2. customThe reaction was then quenched with saturated ammonium chloride solution (50 ml)
  3. customthe layers were separated
  4. extractionThe aqueous layer was further extracted with dichloromethane (2×50 ml)
  5. washthe combined organic layers were washed with brine (2×50 ml)
  6. customdried
  7. customevaporated in vacuo
  8. customThe residual solid (1.8 g) was purified by FCC
  9. washeluting with dichloromethane

Sources & evidence

ORD record
ord-8624fd7b9ceb4e7b953ea49129d4f856
Source dataset
uspto-grants-1990_04
Patent number
US04918080

Reaction notes

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