Benzoylacetone → 1H-Pyrazole,3-methyl-5-phenyl-

HRID 1181032Notes

Reaction equation

HRID 1181032 reaction equation
O.[NH2:2][NH2:3].[C:4]([CH2:12][C:13](=O)[CH3:14])(=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(O)C>[CH3:14][C:13]1[NH:3][N:2]=[C:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:12]=1

Participants

4

Reactant 2

HCID 7166BenzoylacetoneHCID 24654Hydrazine hydrate (1:1)2×

Product 1

HCID 187741H-Pyrazole,3-methyl-5-phenyl-Yield 155.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine hydrate (9.0 mL, 99 mmol, 35 wt. % in H2O; 0.64 equiv) was added to a solution of benzoylacetone (25.00 g, 154.1 mmol, 1 equiv) in ethanol (250 mL). After stirring 14 h, more hydrazine hydrate (8.0 mL, 88 mmol, 0.57 equiv) was added. After 2 h, the reaction solution was concentrated (95° C.) to give the title compound as a white solid (24.31 g, 99.7%). HRMS Calculated for C10H11N2: m/z 159.0922. Found: 159.0917.

Workup

  1. waitAfter 2 h
  2. concentrationthe reaction solution was concentrated (95° C.)

Sources & evidence

ORD record
ord-02ef0defa7804f39892c51bcd55547a5
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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