Phenylhydrazine → 5-(4-Methoxyphenyl)-2-phenyl-2,4-dihydro-3H-pyrazol-3-one

HRID 531188Notes

Reaction equation

HRID 531188 reaction equation
C(O[C:4](=[O:16])[CH2:5][C:6](=O)[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)C.[C:17]1([NH:23][NH2:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[CH3:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([C:6]2[CH2:5][C:4](=[O:16])[N:23]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:24]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 76150Benzenepropanoic acid, 4-methoxy-beta-oxo-, ethyl ester

Product 1

HCID 103081595-(4-Methoxyphenyl)-2-phenyl-2,4-dihydro-3H-pyrazol-3-oneYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using General Procedure A; ethyl-4-methoxybenzoylacetate (7.00 g, 27.8 mmol, 1.1 equ.) in ethanol (100 mL) was treated at 0° C. with phenylhydrazine (2.50 mL, 25.3 mmol, 1.0 equ.) to give 3-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-5(4H)-one (5.21 g, 19.6 mmol, 78%) after crystallization (ethanol) as a light yellow solid. 1H-NMR (400 MHz) CDCl3: 7.99-7.97 (d, 1H), 7.66-7.64 (d, 2H), 7.44-7.40 (t, 2H), 7.22-7.18 (t, 1H), 6.94-6.92 (d, 2H), 3.82 (s, 3H), 3.68 (s, 3H), 13C-NMR (100 MHz) CDCl3: 170.1, 161.5, 154.4, 138.2, 128.8, 127.5, 125.0, 123.5, 118.8, 114.2, 55.3, 39.6; LC/MS-MS: 267.0→77.2 m/z; GS1 and GS2 at 30, DP=81, CE=65, CXP=4, tR=4.15 min.

Sources & evidence

ORD record
ord-083e6ed019f24ad8a47d422efdf5a1e2
Source dataset
uspto-grants-2016_05
Patent number
US09353121B2

Reaction notes

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