Dimethylformamide → 3-(5-Nitrofuran-2-yl)-1-(pyridin-2-yl)-1H-pyrazole-4-carbaldehyde

HRID 839234Notes

Reaction equation

HRID 839234 reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17][N:18]=[C:19]([C:21]1[O:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=1)[CH3:20].N1C=C(C=[N+](C)C)[CH:31]=N1>O>[N+:26]([C:23]1[O:22][C:21]([C:19]2[C:20]([CH:8]=[O:9])=[CH:31][N:17]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][N:11]=3)[N:18]=2)=[CH:25][CH:24]=1)([O-:28])=[O:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 203259884-PyrazolylmethylenedimethylammoniumHCID 867357475-Nitro-2-acetylfuran-(2-pyridyl)hydrazone

Product 1

HCID 203261643-(5-Nitrofuran-2-yl)-1-(pyridin-2-yl)-1H-pyrazole-4-carbaldehydeYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add 9.4 g of phosphorus oxychloride dropwise to 16.4 g of anhydrous dimethylformamide at from 10° to 20° C and then stir the obtained reaction mixture for 30 minutes at room temperature before adding thereto (from 35° to 40° C) 5.0 g of 5-nitro-2-acetylfuran-(2-pyridyl)hydrazone. Stir the thus-prepared admixture for 28 hours under nitrogen at this temperature and then pour it and a solution comprising 4-pyrazolylmethylenedimethylammonium salt onto 250 g of ice and water. Heat the resulting reaction mixture for 2 hours at from 30° to 40° C, draw off the formed precipitate and wash the precipitate with water to obtain a 45% yield of 3-(5-nitro-2-furyl)-1-(2-pyridyl)pyrazole-4-carboxaldehyde [m.p. 191° to 191.5° C (from toluene)].

Workup

  1. customthe obtained reaction mixture for 30 minutes at room temperature
  2. additionbefore adding
  3. stirringStir the thus-prepared admixture for 28 hours under nitrogen at this temperature
  4. additionpour it
  5. temperatureHeat
  6. customthe resulting reaction mixture for 2 hours at from 30° to 40° C
  7. washwash the precipitate with water

Sources & evidence

ORD record
ord-e0bd53e65eea4ed39728d9a0c228553c
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Reaction notes

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