Hydrazine hydrate (1:1) → 5-(4-Methoxyphenyl)-2,4-dihydro-3H-pyrazol-3-one

HRID 855703Notes

Reaction equation

HRID 855703 reaction equation
CO[C:3]1[CH:4]=[C:5]([C:11]2[CH2:15][C:14](=[O:16])[NH:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(OC(=O)CC(=O)C1C=CC(OC)=CC=1)C.O.NN>>[CH3:10][O:9][C:8]1[CH:3]=[CH:4][C:5]([C:11]2[CH2:15][C:14](=[O:16])[NH:13][N:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 76150Benzenepropanoic acid, 4-methoxy-beta-oxo-, ethyl esterHCID 152835193-(3,4-dimethoxyphenyl)-4,5-dihydro-1H-pyrazol-5-one

Product 1

HCID 6053665-(4-Methoxyphenyl)-2,4-dihydro-3H-pyrazol-3-oneYield 67%

Procedure

The starting material was prepared using an analogous procedure to that described for the synthesis of 3-(3,4-dimethoxyphenyl)-4,5-dihydro-1H-pyrazol-5-one in Example 9. Ethyl-4-methoxybenzoylacetate (1 g, 4.5 mmol) was reacted with hydrazine hydrate (218 μl, 4.5 mmol) to give 3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-5-one (570 mg, 67%).

Workup

  1. customThe starting material was prepared

Sources & evidence

ORD record
ord-811a42c16e6949a19fc5de471fb43827
Source dataset
uspto-grants-2007_08
Patent number
US07262201B1

Reaction notes

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