Methylhydrazine → 1,3-dimethyl-4,5,6,7-tetrahydro-1H-indazol-4-one

HRID 569904

Reaction equation

HRID 569904 reaction equation
[CH3:1][NH:2][NH2:3].[C:4]([CH:7]1[C:12](=[O:13])[CH2:11][CH2:10][CH2:9][C:8]1=O)(=O)[CH3:5]>CO>[CH3:1][N:2]1[C:8]2[CH2:9][CH2:10][CH2:11][C:12](=[O:13])[C:7]=2[C:4]([CH3:5])=[N:3]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 1381042-Acetyl-1,3-cyclohexanedione

Product 1

HCID 141266791,3-dimethyl-4,5,6,7-tetrahydro-1H-indazol-4-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 11 ml of methylhydrazine in 50 ml of methanol was added dropwise to an ice-cold solution of 30 grams of 2-acetyl-1,3-cyclohexanedione in 200 ml of methanol and the reaction mixture was heated at reflux for 90 minutes. The solvent was removed under reduced pressure and the residue was triturated in hexane and cooled to give a clammy tan solid. This crude product was recrystallized from a mixture of toluene and hexane to give 1,5,6,7-tetrahydro-1,3-dimethyl-4H-indazol-4-one as a yellow crystalline solid melting at about 82.5°-84° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 90 minutes
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was triturated in hexane
  5. temperaturecooled
  6. customto give a clammy tan solid
  7. customThis crude product was recrystallized from a mixture of toluene and hexane

Sources & evidence

ORD record
ord-4a3ea2c7e75242039f3cd0d7e751f1a0
Source dataset
uspto-grants-1988_03
Patent number
US04734430

Linked notes

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