3-(4'-Fluoro-4-biphenylyl)-3-hydroxybutyric acid hydrazide → 3-(4'-Fluoro-4-biphenylyl)-3-methyl-pyrazolidin-5-one

HRID 1576418Notes

Reaction equation

HRID 1576418 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](O)([CH3:20])[CH2:15][C:16]([NH:18][NH2:19])=[O:17])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3([CH3:20])[CH2:15][C:16](=[O:17])[NH:18][NH:19]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 681401883-(4'-Fluoro-4-biphenylyl)-3-hydroxybutyric acid hydrazide

Product 1

HCID 215126753-(4'-Fluoro-4-biphenylyl)-3-methyl-pyrazolidin-5-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

28.8 g of 3-(4'-fluoro-4-biphenylyl)-3-hydroxybutyric acid hydrazide [obtainable by Friedel-Crafts acetylation of 4-fluorobiphenyl to give 4-p-fluorophenylacetophenone, reaction with bromoacetic acid ethyl ester/zinc to give 3-(4'-fluoro-4-biphenylyl)-3-hydroxybutyric acid ethyl ester and reaction with hydrazine hydrate in ethanol] in 200 ml of DMF is heated and worked up in the customary manner to give 3-(4'-fluoro-4-biphenylyl)-3-methyl-pyrazolidin-5-one, m.p. 194°-196°.

Sources & evidence

ORD record
ord-877f93d772b24cf982b416adca95d036
Source dataset
uspto-grants-1976_09
Patent number
US03980795

Reaction notes

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