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

HRID 1523665Notes

Reaction equation

HRID 1523665 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). 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. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8454a3e84e854189a8f1b1927c3f3a99
Source dataset
uspto-grants-2015_07
Patent number
US09079890B2

Reaction notes

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