Methylhydrazine → 3H-Pyrazol-3-one, 2,4-dihydro-2-methyl-5-phenyl-

HRID 531184Notes

Reaction equation

HRID 531184 reaction equation
[C:1]([CH2:9][C:10]([O:12]CC)=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][NH:16][NH2:17]>C(O)C>[CH3:15][N:16]1[C:10](=[O:12])[CH2:9][C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:17]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 7170Ethyl benzoylacetate

Product 1

HCID 1425623H-Pyrazol-3-one, 2,4-dihydro-2-methyl-5-phenyl-Yield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

According to General Procedure A; ethyl benzoylacetate (18.4 mL, 95.5 mmol, 1.1 equ.) in ethanol (180 mL) was treated at 0° C. with methylhydrazine (4.57 mL, 86.8 mmol, 1.0 equ.) to give 1-methyl-3-phenyl-1H-pyrazol-5(4H)-one (11.0 g 63.1 mmol, 73%) after purification by crystallization (ethanol) as a light yellow solid. 1H-NMR (400 MHz) CDCl3: 7.67-7.65 (m, 2H), 7.42-7.41 (m, 3H), 3.60 (s, 2H), 3.41 (s, 3H), 13C-NMR (100 MHz) CDCl3: 171.8, 154.2, 131.0, 130.3, 128.8, 125.6, 37.9, 31.4. LC/MS-MS: 175.0→77.2 m/z; GS1 and GS2 at 30, DP=66, CE=43, CXP=4, tR=3.45 min.

Sources & evidence

ORD record
ord-fa3d24eca639409ca87d0116ca8a3586
Source dataset
uspto-grants-2016_05
Patent number
US09353121B2

Reaction notes

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