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

HRID 1511109Notes

Reaction equation

HRID 1511109 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. Methylhydrazine (39.90 ml, 750.1 mmol) in ethanol (150 mL) was added, and the reaction was stirred at ambient temperature for 2 hours, then 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-2f2d89c48a4f49b5b7dccb09cfedb4b6
Source dataset
uspto-grants-2012_07
Patent number
US08212045B2

Reaction notes

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