Methane → HCID 14128507, compound

HRID 569899Notes

Reaction equation

HRID 569899 reaction equation
[NH2:1]N.C[N:4]([CH:6]=[C:7]1[C:15](=O)[CH2:14][CH2:13][C:12]2[N:11]([CH3:17])[N:10]=[CH:9][C:8]1=2)C.C>CO>[CH3:17][N:11]1[C:12]2[CH2:13][CH2:14][C:15]3[NH:1][N:4]=[CH:6][C:7]=3[C:8]=2[CH:9]=[N:10]1

Participants

5

Reactant 3

HCID 297MethaneHCID 9321HydrazineHCID 54528014HCID 54528014, compound

Product 1

HCID 14128507HCID 14128507, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrazine (1.00 ml) was added dropwise to a solution of 4.1 g of 4-[(dimethylamino)methylene]-1,4,6,7-tetrahydro-1-methyl-5H-indazol-5-one in 100 ml of methanol. The solution was heated at reflux for 30 minutes and treated with a small amount of activated charcoal. The mixture was gravity-filtered and the filtrate was concentrated in vacuo. The residue was flash chromatograhed (10% methanol in dichloromethane) on silica gel to provide an amber syrup. The syrup was triturated with ether to afford 3,4,5,6-tetrahydro-3-methylbenzo[1,2-c:4,3-c']dipyrazole as tan crystals (74% yield). Recrystallization from toluene gave a solid melting at about 150°-156° C.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 30 minutes
  3. filtrationThe mixture was gravity-filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customto provide an amber syrup
  6. customThe syrup was triturated with ether

Sources & evidence

ORD record
ord-d24cbf286089433eb550b8ebf8b5b2c5
Source dataset
uspto-grants-1988_03
Patent number
US04734429

Reaction notes

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