Methylhydrazine → 1-Methyl-1,5,6,7-tetrahydro-4H-indazol-4-one

HRID 129483

Reaction equation

HRID 129483 reaction equation
[CH3:1][NH:2][NH2:3].CN([CH:7]=[C:8]1[C:13](=[O:14])[CH2:12][CH2:11][CH2:10][C:9]1=O)C>CO>[CH3:1][N:2]1[C:9]2[CH2:10][CH2:11][CH2:12][C:13](=[O:14])[C:8]=2[CH:7]=[N:3]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 3593532-[(Dimethylamino)methylidene]cyclohexane-1,3-dione

Product 1

HCID 27657961-Methyl-1,5,6,7-tetrahydro-4H-indazol-4-oneYield 89.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 46.1 g (1.0 mol) of methylhydrazine in 400 ml of methanol is slowly added dropwise at ambient temperature to a solution of 167.2 g (1.0 mol) of 2-(dimethylaminomethylene)-cyclohexane-1,3-dione in 2000 ml of methanol. The reaction mixture is then refluxed for 1.5 hours. It is evaporated dryness in vacuo and the crude product obtained is purified by chromatography on silica gel (made by Baker, 30-60 μm) with a mixture of ethyl acetate and cyclohexane=9:1.

Workup

  1. temperatureThe reaction mixture is then refluxed for 1.5 hours
  2. customIt is evaporated dryness in vacuo

Sources & evidence

ORD record
ord-f8c27671b78c49e7a431f3776f2924a6
Source dataset
uspto-grants-1995_11
Patent number
US05468766

Linked notes

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