Methylhydrazine → HCID 14126717, compound

HRID 569916Notes

Reaction equation

HRID 569916 reaction equation
O[CH:2]=[C:3]1[C:13](=O)[C:8]2[CH:9]=[N:10][N:11]([CH3:12])[C:7]=2[CH2:6][CH2:5][CH2:4]1.[CH3:15][NH:16][NH2:17]>CO>[CH3:15][N:16]1[C:13]2[C:8]3[CH:9]=[N:10][N:11]([CH3:12])[C:7]=3[CH2:6][CH2:5][CH2:4][C:3]=2[CH:2]=[N:17]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 57144783HCID 57144783, compound

Product 1

HCID 14126717HCID 14126717, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To an ice-cold solution of 4 g of 5,6,7,8-tetrahydro-5-hydroxymethylene-1-methyl-4(1H) cycloheptapyrazolone in 130 ml of methanol was added, dropwise, a solution of 1.1 ml of methylhydrazine in 20 ml of methanol and the mixture was heated at reflux for 2.5 hours. Removal of the solvent under reduced pressure left a residual dark oil. The oil was flash chromatographed (7.5% 2-propanol in methylene chloride) to give 4,5,6,7-tetrahydro-1,7-dimethyl-1H-cyclohepta[1,2-c:3,4-c']dipyrazole as a yellow crystalline solid melting at about 94°-96° C. The chromatography also gave 4,5,6-tetrahydro-2,7-dimethyl-2H-cyclohepta[1,2-c:3,4-c')]dipyrazole melting at about 119°-121° C.

Workup

  1. temperatureat reflux for 2.5 hours
  2. customRemoval of the solvent under reduced pressure
  3. waitleft a residual dark oil
  4. customchromatographed (7.5% 2-propanol in methylene chloride)

Sources & evidence

ORD record
ord-e7ab0047f2c3405a85c71366d4f09277
Source dataset
uspto-grants-1988_03
Patent number
US04734430

Reaction notes

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