Hydrazine hydrate (1:1) → 3-(4'-Fluoro-4-biphenylyl)-3-methyl-pyrazolidin-5-one

HRID 1576422Notes

Reaction equation

HRID 1576422 reaction equation
C([O:3][C:4](=O)[CH:5]=[C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)[CH3:7])C.O.[NH2:23][NH2:24]>C(O)C>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:6]3([CH3:7])[CH2:5][C:4](=[O:3])[NH:24][NH:23]3)=[CH:9][CH:10]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 570642923-(4'-Fluoro-4-biphenylyl)-2-butenoic acid ethyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 28.4 g of 3-(4'-fluoro-4-biphenylyl)-2-butenoic acid ethyl ester [obtainable by dehydrating 3-(4'-fluoro-4-biphenylyl)-3-hydroxybutyric acid ethyl ester employing p-toluenesulfonic acid] and 25 g of hydrazine hydrate (100% strength) in 400 ml of ethanol is boiled for 18 hours. The mixture is cooled, poured onto ice water and worked up in the usual manner to give 3-(4'-fluoro-4-biphenylyl)-3-methyl-pyrazolidin-5-one, m.p. 194°-196°.

Workup

  1. temperatureThe mixture is cooled
  2. additionpoured onto ice water

Sources & evidence

ORD record
ord-8e960e644d0b464eaab7e60915290631
Source dataset
uspto-grants-1976_09
Patent number
US03980795

Reaction notes

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