4-Methylphenylhydrazine monohydrochloride → 1-(4-Methylphenyl)pyrazolidin-3-one

HRID 906483Notes

Reaction equation

HRID 906483 reaction equation
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.C1CCN2C(=NCCC2)CC1.Br[CH2:23][CH2:24][C:25](Cl)=[O:26]>C(Cl)Cl>[CH3:10][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:23][CH2:24][C:25](=[O:26])[NH:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 125044-Methylphenylhydrazine monohydrochlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 84944Propanoyl chloride, 3-bromo-

Product 1

HCID 19134851-(4-Methylphenyl)pyrazolidin-3-oneYield 19,455.801%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

10 g of p-tolylhydrazine hydrochloride are dissolved in 100 ml of anhydrous CH2Cl2. The solution is cooled to 0° C. and 19 ml of DBU and then 6.5 mg of 3-bromopropionyl chloride are added. The mixture is stirred at ambient temperature for one hour. The reaction medium is poured onto water, extraction is carried out with CH2Cl2 and then purification is carried out by chromatography on a silica column eluted with an AcOEt/petroleum ether (v/v; 50/50) mixture. 1.3 g of crystals are obtained.

Workup

  1. additionThe reaction medium is poured onto water, extraction
  2. custompurification
  3. washeluted with an AcOEt/petroleum ether (v/v; 50/50) mixture

Sources & evidence

ORD record
ord-af986a9ec0764771a06819006f7a150d
Source dataset
uspto-grants-2011_09
Patent number
US08012991B2

Reaction notes

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