Ammonia → 5-(5-nitrofuran-2-yl)-1H-pyrazole-4-carbaldehyde

HRID 839198Notes

Reaction equation

HRID 839198 reaction equation
COC([N:5]1[CH:9]=[C:8]([CH:10]=[O:11])[C:7]([C:12]2[O:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=2)=[N:6]1)=O.N.Cl>O1CCOCC1>[N+:17]([C:14]1[O:13][C:12]([C:7]2[C:8]([CH:10]=[O:11])=[CH:9][NH:5][N:6]=2)=[CH:16][CH:15]=1)([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 203259421-Methoxycarbonyl-3-(5-nitro-2-furyl)pyrazole-4-carboxaldehyde

Product 1

HCID 1785198815-(5-nitrofuran-2-yl)-1H-pyrazole-4-carbaldehydeYield 78%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 9.1 g of 1-methoxycarbonyl-3-(5-nitro-2-furyl)pyrazole-4 -carboxaldehyde in 80 ml of dioxan add dropwise at 5° to 8° C 33.4 ml of concentrated ammonia solution. Stirr the resulting admixture for 15 minutes before acidifying it with 2N hydrochloric acid to a pH value of 2. Distill off the greater part of the dioxan in vacuo. Mix the residue with 100 ml of water. Draw off the precipitate and wash it with water to obtain 3-(5-nitro-2-furyl)-1H-pyrazole-4-carboxaldehyde [melting point: 179° to 185° C] with a yield of 78%.

Workup

  1. distillationDistill off the greater part of the dioxan in vacuo
  2. additionMix the residue with 100 ml of water
  3. washwash it with water

Sources & evidence

ORD record
ord-8b34e1555d6848df8c43feb61b445c64
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Reaction notes

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