Methylhydrazine → 1-Methyl-4-(4-methylphenyl)-1H-pyrazole

HRID 2307348Notes

Reaction equation

HRID 2307348 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:11]=O)[CH:9]=O)=[CH:4][CH:3]=1.[CH3:13][NH:14][NH2:15]>C(O)C>[CH3:13][N:14]1[CH:11]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[CH:9]=[N:15]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 27369302-(4-Methylphenyl)malondialdehyde

Product 1

HCID 43190701-Methyl-4-(4-methylphenyl)-1H-pyrazoleYield 89.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(4-methylphenyl)-malondialdehyde (3.05 g), absolute ethanol (40 ml), and methylhydrazine (1.09 g) was stirred at room temperature for 18 hours and the volatiles removed at room temperature. Water was added and the mixture was extracted with dichloromethane. After drying over anhydrous sodium sulfate, the solution was filtered through a short column of hydrous sodium magnesium silicate and further eluted with several volumes of dichloromethane. The combined organic phase was concentrated on a steam bath with the gradual addition of hexane until crystallization occurred. After cooling, the crystals were collected by filtration to yield the title compound (2.91 g), m.p. 107-108° C.

Workup

  1. customthe volatiles removed at room temperature
  2. additionWater was added
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. filtrationthe solution was filtered through a short column of hydrous sodium magnesium silicate
  6. washfurther eluted with several volumes of dichloromethane
  7. concentrationThe combined organic phase was concentrated on a steam bath with the gradual addition of hexane until crystallization
  8. temperatureAfter cooling
  9. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-62fbe4d531c948ed8520e4ad774f39d7
Source dataset
uspto-grants-2004_12
Patent number
US06831079B1

Reaction notes

Loading…