Methylhydrazine → 1,3,5-trimethyl-1H-pyrazol-4-yl benzoate

HRID 1511118Notes

Reaction equation

HRID 1511118 reaction equation
[C:1]([O:9][CH:10]([C:14](=O)[CH3:15])[C:11](=O)[CH3:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][NH:18][NH2:19]>C(O)C>[C:1]([O:9][C:10]1[C:14]([CH3:15])=[N:19][N:18]([CH3:17])[C:11]=1[CH3:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 207383-(Benzoyloxy)-2,4-pentanedione

Product 1

HCID 674866031,3,5-trimethyl-1H-pyrazol-4-yl benzoateYield 92.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A flask was charged with 2,4-dioxopentan-3-yl benzoate (82.59 g, 375.0 mmol) and ethanol (1.5 L) was added. To this solution was added methylhydrazine (39.90 ml, 750.1 mmol) in ethanol (150 mL). The reaction was stirred at ambient temperature for 2 hours and concentrated in vacuo to afford 1,3,5-trimethyl-1H-pyrazol-4-yl benzoate (80 g, 92.6% yield).

Workup

  1. additionwas added
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5c315d1afbc64476ba39386763355688
Source dataset
uspto-grants-2012_07
Patent number
US08212045B2

Reaction notes

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