Phenylhydrazine → HCID 89650063, compound

HRID 531187Notes

Reaction equation

HRID 531187 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:6]([CH2:8][C:9]([O:11]CC)=O)=O.[C:19]1([NH:25][NH2:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]2[CH2:8][C:9](=[O:11])[N:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:26]=2)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 2758465Ethyl 3,4-dimethoxybenzoylacetate

Product 1

HCID 89650063HCID 89650063, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using General Procedure A; ethyl 3,4-dimethoxybenzoylacetate (3.00 g, 11.9 mmol, 1.1 equ.) in ethanol (60 mL) was treated at 0° C. with phenylhydrazine (1.17 mL, 10.8 mmol, 1.0 equ.) to afford 3-(3,4-dimethoxyphenyl)-1-phenyl-1H-pyrazol-5(4H)-one (920 mg, 2.32 mmol, 22%) after purification by crystallization (ethanol) as a yellow powder. 1H-NMR (400 MHz) CDCl3: 8.00-7.97 (d, 1H), 7.48-7.42 (m, 3H), 7.25-7.21 (t, 1H), 7.17-7.14 (dd, 1 H), 6.91-6.89 (d, 1H), 3.98 (s, 3H), 3.95 (s, 3H), 3.83 (s, 2H), 13C-NMR (100 MHz) CDCl3: 170.1, 154.4, 151.4, 149.4, 138.1, 128.8, 125.2, 123.8, 120.1, 119.1, 110.7, 107.6, 56.0, 56.0, 39.7; LC/MS-MS: 297.0→218.2 m/z; GS1 and GS2 at 30, DP=96, CE=37, CXP=18, tR=3.98 min.

Sources & evidence

ORD record
ord-2862e03bc52f4f4097a7067c4d00750d
Source dataset
uspto-grants-2016_05
Patent number
US09353121B2

Reaction notes

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