Methylhydrazine → 115309-88-1

HRID 569905Notes

Reaction equation

HRID 569905 reaction equation
[C:1]([CH:4]1[C:10](=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=O)(=O)C.[CH3:13][NH:14][NH2:15]>CO>[CH3:13][N:14]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[CH:1]=[N:15]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 15535129HCID 15535129, compound

Product 1

HCID 20146596115309-88-1

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To an ice-cold solution of 21 grams of 2-acetyl-1,3-cycloheptanedione in 180 ml of methanol was added, dropwise, a solution of 6.2 ml of methylhydrazine in 30 ml of methanol. The resulting reaction mixture was heated at reflux for 1 hour and the solvent was then removed under reduced pressure. The residual material was partitioned between dichloromethane and brine, the aqueous layer was extracted twice with dichloromethane, and the combined organic layers were dried over magnesium sulfate. The solvent was removed under reduced pressure to leave a dark oil which crystallized on standing. The solid was recrystallized from a mixture of ether and hexane to give 5,6,7,8-tetrahydro-1-methyl-4(1H)-cycloheptapyrazolone as a yellow crystalline solid melting at about 95°-97° C.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for 1 hour
  4. customthe solvent was then removed under reduced pressure
  5. customThe residual material was partitioned between dichloromethane and brine
  6. extractionthe aqueous layer was extracted twice with dichloromethane
  7. dry with materialthe combined organic layers were dried over magnesium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customto leave a dark oil which
  10. customcrystallized
  11. customThe solid was recrystallized from a mixture of ether and hexane

Sources & evidence

ORD record
ord-2fa7a2ac0b36493997f3427480ac01ef
Source dataset
uspto-grants-1988_03
Patent number
US04734430

Reaction notes

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