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

HRID 1679760

Reaction equation

HRID 1679760 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 2 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/dimethyl formamide mixture.

Workup

  1. customrose to 55° C
  2. temperatureAfter heating the reaction solution for 2 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/dimethyl formamide mixture

Sources & evidence

ORD record
ord-caaeb24f5322455ca920835719684400
Source dataset
uspto-grants-1978_03
Patent number
US04081596

Linked notes

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