Dimethylformamide → 1-Phenyl-1H-pyrazole-4-carbaldehyde

HRID 1177922Notes

Reaction equation

HRID 1177922 reaction equation
[C:1]1([N:7]2[CH:11]=[CH:10][CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN([CH:15]=[O:16])C.O=P(Cl)(Cl)Cl>>[C:1]1([N:7]2[CH:11]=[C:10]([CH:15]=[O:16])[CH:9]=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 707691-Phenylpyrazole

Product 1

HCID 9520891-Phenyl-1H-pyrazole-4-carbaldehydeYield 112.7%

Conditions

Temperature
106 °C

Procedure

1-Phenyl-1H-pyrazole (250 mg, 1.7 mmol) was added to a cold (0-4° C.) solution of DMF (1.5 g, 1.6 mL, 9.7 mmol) and POCl3 (1.86 g, 1.1 mL, 19.2 mmol) and stirring continued for 10 minutes. The resulting mixture was heated at 106° C. for 2.5 hrs. The reaction mixture was cooled and quenched with ice cold water, basified with 20% aqueous NaOH solution, filtered the solid precipitated to afford 330 mg (crude) of 1-Phenyl-1H-pyrazole-4-carbaldehyde. 1H NMR (CDCl3): δ 10.0 (s, 1H), 8.45 (s, 1H), 8.2 (s, 1H), 7.75 (d, 2H), 7.55 (t, 2H), 7.45 (t, 1H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customquenched with ice cold water
  3. filtrationfiltered the solid
  4. customprecipitated

Sources & evidence

ORD record
ord-2617b152150842f4b8b98bc15f74914f
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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