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

HRID 133177

Reaction equation

HRID 133177 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-e0d1fe6a07a74c78a3121edd965e5815
Source dataset
uspto-grants-2008_06
Patent number
US07390818B2

Linked notes

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