Hydrazine hydrate (1:1) → 5-(4-Chloro-phenyl)-2,4-dihydro-pyrazol-3-one

HRID 1683810Notes

Reaction equation

HRID 1683810 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8](C)(C)[C:9](OCC)=[O:10])=O)=[CH:4][CH:3]=1.O.[NH2:19][NH2:20]>C(O)C>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]2[CH2:8][C:9](=[O:10])[NH:20][N:19]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 16638375HCID 16638375, compound

Product 1

HCID 47787935-(4-Chloro-phenyl)-2,4-dihydro-pyrazol-3-oneYield 82,212.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 26 g (0.10 mmol) of ethyl α-(4-chlorobenzoyl)isobutyrate, 10 g (0.20 mmol) of hydrazine monohydrate and 200 ml of ethanol was heated under reflux for 18 hours. The reaction solution was concentrated under reduced pressure. The obtained crude product was washed successively with water, methanol-water and diethyl ether-n-hexane, and then air dried to give 16 g of the object compound as white crystals (yield 84%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. customThe obtained crude product
  5. washwas washed successively with water, methanol-water and diethyl ether-n-hexane
  6. customair dried

Sources & evidence

ORD record
ord-5449332995294ab599caac6f51e011c8
Source dataset
uspto-grants-1997_06
Patent number
US05639776

Reaction notes

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