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

HRID 1523646Notes

Reaction equation

HRID 1523646 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-75ead23bdb4f454bbbdb31bb9c5adb3f
Source dataset
uspto-grants-2015_07
Patent number
US09079890B2

Reaction notes

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