Phenylhydrazine → 1H-Indole, 3-butyl-2-methyl-

HRID 1646410Notes

Reaction equation

HRID 1646410 reaction equation
[C:1]1([NH:7]N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S([O-])(O)(=O)=O.[Na+].[CH3:15][C:16](=O)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>O>[CH3:15][C:16]1[NH:7][C:1]2[C:6]([C:17]=1[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:5][CH:4]=[CH:3][CH:2]=2

Participants

5

Reactant 3

HCID 7516PhenylhydrazineHCID 80512-HeptanoneHCID 516919Sodium Bisulfate

Product 1

HCID 122748871H-Indole, 3-butyl-2-methyl-Yield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

27 g (0.25 mol) of phenylhydrazine were initially introduced at 90° C. in a solution of 1.12 mol of sodium hydrogen sulphate in 420 ml of water. 30 g (0.263 mol) of heptan-2-one were metered in in the course of 30 min. This mixture was stirred for 7 h at 100° C. After cooling, the batch was neutralised and the organic phase was separated off and distilled. 2-Methyl-3-butylindole was obtained in a yield of 62%.

Workup

  1. customwere metered in in the course of 30 min
  2. temperatureAfter cooling
  3. customthe organic phase was separated off
  4. distillationdistilled

Sources & evidence

ORD record
ord-d3837871a81a4b5dab63332022b82b89
Source dataset
uspto-grants-1993_01
Patent number
US05179211

Reaction notes

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