1-Propanol → 3-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazole

HRID 1607205Notes

Reaction equation

HRID 1607205 reaction equation
C1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13](=[CH2:23])[C:14]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=O)C=CC=CC=1.C(O)CC.O.[NH2:29][NH2:30]>CO>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]2[CH:13]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:7]=3)[CH2:23][NH:30][N:29]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 10311-PropanolHCID 24654Hydrazine hydrate (1:1)HCID 67944782HCID 67944782, compound

Product 1

HCID 113688843-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 500 ml round bottomed flask equipped with a reflux condensor was mixed 98 g of 2-phenyl 4'-chlorophenyl acrylophenone (0.40 mole), 200 ml n-propanol, and 50 ml hydrazine monohydrate (1.0 mole). The mixture was refluxed for 1 hour, cooled slightly and 100 ml of methanol added. The resulting solution was cooled in an ice bath and the resulting solid filtered and washed twice with cold ethyl ether yielding 55 g of a white solid. mp 156°-162° C. NMR data was consistent with the structure.

Workup

  1. customIn a 500 ml round bottomed flask equipped with a reflux condensor
  2. temperatureThe mixture was refluxed for 1 hour
  3. temperaturecooled slightly
  4. temperatureThe resulting solution was cooled in an ice bath
  5. filtrationthe resulting solid filtered
  6. washwashed twice with cold ethyl ether yielding 55 g of a white solid

Sources & evidence

ORD record
ord-26e16f2a17534a21ac0b4d8e4373a34d
Source dataset
uspto-grants-1989_09
Patent number
US04863947

Reaction notes

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