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

HRID 534099Notes

Reaction equation

HRID 534099 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-a616ae5253064eaab458bbed872ecb2a
Source dataset
uspto-grants-2014_10
Patent number
US08853409B2

Reaction notes

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