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

HRID 978156Notes

Reaction equation

HRID 978156 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.

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-cce17d5c59f745f89215e32c1cebd9ed
Source dataset
uspto-grants-1987_05
Patent number
US04663341

Reaction notes

Loading…