Water → 6-Ethyl-1-methyl-1H-indole

HRID 442756Notes

Reaction equation

HRID 442756 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11](=O)[CH3:12])[CH:9]=2)[CH:4]=[CH:3]1.O.NN.[OH-].[K+].O>C(O)COCCO>[CH2:11]([C:8]1[CH:9]=[C:10]2[C:5]([CH:4]=[CH:3][N:2]2[CH3:1])=[CH:6][CH:7]=1)[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 538738741-(1-Methyl-1H-indol-6-yl)ethan-1-one

Product 1

HCID 543303436-Ethyl-1-methyl-1H-indoleYield 96.3%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
62 °C

Procedure

A mixture of 0.226 g 1-(1-methyl-1H-indol-6-yl)-ethanone, 1.35 mL of 85% hydrazine hydrate, 0.88 g of potassium hydroxide in 15 mL of diethylene glycol was stirred at 62° C. over night. The reaction mixture was cooled, poured into water and extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate and concentrated to give 0.200 g of 6-ethyl-1-methylindole as a colorless oil after chromatographic purification on a silica gel column.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3c8a457762d0495eadb1c9e76d7d24f0
Source dataset
uspto-grants-1999_04
Patent number
US05891901

Reaction notes

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