Ethyl acetylphenylacetate → 3-Methyl-4-phenyl-1-(alpha-methyl-3,4-dichlorobenzyl)-5-pyrazolone

HRID 1415595

Reaction equation

HRID 1415595 reaction equation
C(O[C:4](=[O:15])[CH:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:6]([CH3:8])=O)C.[CH3:16][CH:17]([NH:26][NH2:27])[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=1>C(O)C>[CH3:8][C:6]1[NH:27][N:26]([CH:17]([CH3:16])[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)[C:4](=[O:15])[C:5]=1[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 95389Ethyl acetylphenylacetateHCID 3016950(1-(3,4-Dichlorophenyl)ethyl)hydrazine

Product 1

HCID 203358943-Methyl-4-phenyl-1-(alpha-methyl-3,4-dichlorobenzyl)-5-pyrazolone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

20.6 g of α-phenylacetoacetic acid ethyl ester were added dropwise under nitrogen to a solution of 20.5 g (0.1 mol) of α-methyl-3,4-dichlorobenzylhydrazine in 20 ml of absolute ethanol, during which the temperature of the reaction mixture rose to 55° C. After heating the reaction solution for two hours under reflux, the reaction product crystallized out on cooling the reaction mixture. The crystals were filtered off, rinsed with ether and recrystallized from an ethanol/dimethylformamide mixture.

Workup

  1. customrose to 55° C
  2. temperatureAfter heating the reaction solution for two hours
  3. temperatureunder reflux
  4. customthe reaction product crystallized out
  5. temperatureon cooling the reaction mixture
  6. filtrationThe crystals were filtered off
  7. washrinsed with ether
  8. customrecrystallized from an ethanol/dimethylformamide mixture

Sources & evidence

ORD record
ord-889ffef7cfb042498b216c6a8a715a6b
Source dataset
uspto-grants-1977_01
Patent number
US04005215

Linked notes

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