P-Chloroacetophenone → 5-Chloro-3-(4-chlorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde

HRID 441859Notes

Reaction equation

HRID 441859 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([CH2:8][C:9]([O:11]CC)=O)=O)=[CH:4][CH:3]=1.[Cl:16][C:17]1C=CC(C(=O)C)=CC=1.C(=O)(OCC)OCC.[H-].[Na+].[C:36]1([NH:42][NH2:43])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.ClC1C=CC(C2CC(=O)N(C3C=CC=CC=3)N=2)=CC=1>C(O)C.C(O)(=O)C>[Cl:16][C:17]1[N:42]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:43]=[C:6]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:15][CH:14]=2)[C:8]=1[CH:9]=[O:11]

Participants

9

Reactant 6

HCID 7467P-ChloroacetophenoneHCID 7516PhenylhydrazineHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 101336Ethyl 3-(4-chlorophenyl)-3-oxopropanoateHCID 102860883-(4-Chlorophenyl)-1-phenyl-2-pyrazolin-5-one

Product 1

HCID 214183605-Chloro-3-(4-chlorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

50.8 g of ethyl p-chlorobenzoylacetate (produced for example from p-chloroacetophenone, diethyl carbonate and sodium hydride with a yield of 72 %) 29 g of phenylhydrazine, 5 ml of glacial acetic acid and 150 ml of ethanol are heated in a nitrogen atmosphere for 1 hour at boiling point. After cooling in an ice bath 3-p-chlorophenyl-1-phenyl-2-pyrazoline-5-one is obtained with a yield of 84 %; F 160.5°-161.5°.

Workup

  1. temperatureare heated in a nitrogen atmosphere for 1 hour
  2. customis obtained with a yield of 84 %
  3. customF 160.5°-161.5°

Sources & evidence

ORD record
ord-d83de5859f6d48bcb6586b2b3b97c85c
Source dataset
uspto-grants-1977_08
Patent number
US04042702

Reaction notes

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