Hydrochloric Acid → HCID 20146592, compound

HRID 569914Notes

Reaction equation

HRID 569914 reaction equation
[CH3:1][NH:2][NH2:3].O[CH:5]=[C:6]1[CH2:14][CH2:13][C:12]2[N:11]([CH3:15])[N:10]=[CH:9][C:8]=2[C:7]1=O.[ClH:17]>CO.CCOCC.C(O)C>[ClH:17].[CH3:1][N:2]1[C:7]2[C:8]3[CH:9]=[N:10][N:11]([CH3:15])[C:12]=3[CH2:13][CH2:14][C:6]=2[CH:5]=[N:3]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 6061MethylhydrazineHCID 571627141,5,6,7-Tetrahydro-5-(hydroxymethylene)-1-methyl-4h-indazol-4-one

Product 1

HCID 20146592HCID 20146592, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A solution of 3.2 ml of methylhydrazine in 30 ml of methanol was added dropwise to an ice-cold solution of 10.5 g of 1,5,6,7-tetrahydro-5-hydroxymethylene-1-methyl-4H-indazol-4-one in 200 ml of methanol. The reaction was heated at reflux for 3.5 hours and the solvent was then removed under reduced pressure. The residue was triturated with a mixture of ether and ethanol to give a crude tan solid. This solid was dissolved in a mixture of ether and ethanol and acidified with ethereal hydrogen chloride. The yellow precipitate which formed was separated by filtration and recrystallized from a mixture of ethanol and propanol to give 1,4,5,6-tetrahydro-1,6-dimethylbenzo[1,2-c:3,4-c']dipyrazole monohydrochloride as a yellow crystalline solid melting at about 222°-226° C. with decomposition (51% yield). This compound has the following structural formula: ##STR6##

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 3.5 hours
  3. customthe solvent was then removed under reduced pressure
  4. customThe residue was triturated with a mixture of ether and ethanol
  5. customto give a crude tan solid
  6. customThe yellow precipitate which formed
  7. customwas separated by filtration
  8. customrecrystallized from a mixture of ethanol and propanol

Sources & evidence

ORD record
ord-a80dd788797c4fd3a3a655bf6734bdd7
Source dataset
uspto-grants-1988_03
Patent number
US04734430

Reaction notes

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