3-(4-Chlorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde → 3-(4-Chlorophenyl)-1-phenyl-1H-pyrazole-4-methanol

HRID 2285978Notes

Reaction equation

HRID 2285978 reaction equation
[C:1]1([N:7]2[CH:11]=[C:10]([CH:12]=[O:13])[C:9]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>C(O)C.CN(C)C=O>[OH:13][CH2:12][C:10]1[C:9]([C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)=[N:8][N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:11]=1

Participants

5

Reactant 2

HCID 7034923-(4-Chlorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 7401783-(4-Chlorophenyl)-1-phenyl-1H-pyrazole-4-methanolYield 93.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

80 grams 1-phenyl-3-(p-chlorophenyl)-pyrazol-4-aldehyde were dissolved in a mixture of 800 milliliters ethanol and 1200 milliliters dimethylformamide. To the solution thus obtained, 5.5 grams 95% sodium borohydride were added in small portions at 20°-25° C. The mixture was then stirred for one more hour at room temperature. Thereafter, the reaction mixture was evaporated and the residue was taken up, with rubbing, with ethanol and water were thereafter added. The precipitate formed thereby was separated, dispersed and stirred in warm water, the precipitate was filtered off by suction, dried and recrystallized from benzene. 75 grams 4-hydroxymethyl-1-phenyl-3-(p-chloropheny)-pyrazol, melting at 141°-142° C., were obtained, representing a yield of 93%.

Workup

  1. customTo the solution thus obtained
  2. customThereafter, the reaction mixture was evaporated
  3. additionwere thereafter added
  4. customThe precipitate formed
  5. customthereby was separated
  6. additiondispersed
  7. stirringstirred in warm water
  8. filtrationthe precipitate was filtered off by suction
  9. customdried
  10. customrecrystallized from benzene

Sources & evidence

ORD record
ord-28e4665cb67a4ffa8f6de19327c68a75
Source dataset
uspto-grants-1982_04
Patent number
US04325962

Reaction notes

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