Hydrochloric Acid → 3-(4'-Fluoro-4-biphenylyl)-3-methyl-pyrazolidin-5-one

HRID 1576429Notes

Reaction equation

HRID 1576429 reaction equation
[CH3:1][C:2]1[NH:3][NH:4][C:5](=[O:7])[CH:6]=1.[Mg].Br[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1.Cl>C1COCC1.CCOCC>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:13]2[CH:14]=[CH:15][C:10]([C:2]3([CH3:1])[CH2:6][C:5](=[O:7])[NH:4][NH:3]3)=[CH:11][CH:12]=2)=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 968824-Bromo-4'-fluoro-1,1'-biphenylHCID 3197713H-Pyrazol-3-one, 2,4-dihydro-5-methyl-HCID 5462224Magnesium

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 9.8 g of 3-methyl-pyrazolin-5-one in 100 ml of THF is added dropwise with stirring and cooling, to a Grignard solution prepared from 4.8 g of magnesium and 20.3 g of 4-bromo-4'-fluoro-biphenyl in 800 ml of absolute ether. After stirring for 2 hours at 10°-25°, the mixture is decomposed with ice and dilute hydrochloric acid 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. temperaturecooling, to a Grignard solution
  2. stirringAfter stirring for 2 hours at 10°-25°

Sources & evidence

ORD record
ord-273526f54ead4027bf8c38140a4f142b
Source dataset
uspto-grants-1976_09
Patent number
US03980795

Reaction notes

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