Phenylhydrazine → 3H-Indole, 2,3,3-trimethyl-

HRID 1646402Notes

Reaction equation

HRID 1646402 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+].[CH:15]([C:18]([CH3:20])=O)([CH3:17])[CH3:16]>O>[CH3:20][C:18]1[C:15]([CH3:17])([CH3:16])[C:6]2[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=2)[N:7]=1

Participants

5

Reactant 3

HCID 7516PhenylhydrazineHCID 112513-Methyl-2-butanoneHCID 516919Sodium Bisulfate

Product 1

HCID 154273H-Indole, 2,3,3-trimethyl-Yield 97.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

226 g (2 mol) of phenylhy-drazine (95.7% pure) were initially introduced at 90° C. in a solution of 5 mol of sodium hydrogen sulphate in 1900 ml of water. 225 ml (2.1 mol) of methyl isopropyl ketone were added dropwise in the course of 30 min. The mixture was stirred for 3 h at 90° to 100° C. After cooling, the batch was neutralised and the organic phase was separated off and distilled. 299.3 g of 97.5% pure 2,3,3-trimethylindolenine were obtained Yield: 91.6% of the theoretical yield.

Workup

  1. temperatureAfter cooling
  2. customthe organic phase was separated off
  3. distillationdistilled

Sources & evidence

ORD record
ord-7cbbfff0c62b4ca99801784b33c152f2
Source dataset
uspto-grants-1993_01
Patent number
US05179211

Reaction notes

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