Methylhydrazine → HCID 14126711, compound

HRID 569917Notes

Reaction equation

HRID 569917 reaction equation
[CH3:1][NH:2][NH2:3].[CH3:4][N:5]1[C:13]2[CH2:12][C:11]([CH3:15])([CH3:14])[CH:10]([CH:16]=O)[C:9](=O)[C:8]=2[CH:7]=[N:6]1>CO>[CH3:1][N:2]1[CH:16]=[C:10]2[C:11]([CH3:15])([CH3:14])[CH2:12][C:13]3[N:5]([CH3:4])[N:6]=[CH:7][C:8]=3[C:9]2=[N:3]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 20146597HCID 20146597, compound

Product 1

HCID 14126711HCID 14126711, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 0.59 ml of methylhydrazine in 20 ml of methanol was added dropwise to an ice-cold solution of 2.2 g of 4,5,6,7-tetrahydro-1,6,6-trimethyl-4-oxo-1H-indazole-5-carboxaldehyde in 80 ml of methanol. The solution was heated at reflux for 45 minutes and the solvent was removed under reduced pressure. The residue was dissolved in hot toluene and cooled to provide off-white crystals which were recrystallized from toluene to give 2,4,5,6-tetrahydro-2,4,4,6-tetramethylbenzo[1,2-c:3,4-c']dipyrazole melting at about 172°-173° C. The initial toluene mother liquor was concentrated under reduced pressure to provide tan crystals which were recrystallized from toluene to give 1,4,5,6-tetrahydro-1,4,4,6-tetramethylbenzo[1,2-c:3,4-c']dipyrazole melting at about 105°-108° C.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 45 minutes
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in hot toluene
  5. temperaturecooled
  6. customto provide off-white crystals which
  7. customwere recrystallized from toluene

Sources & evidence

ORD record
ord-49b5eef246c543ec9dc76b48c7c61ebf
Source dataset
uspto-grants-1988_03
Patent number
US04734430

Reaction notes

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