Ammonia → 3-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbonitrile

HRID 839223Notes

Reaction equation

HRID 839223 reaction equation
[N+:1]([C:4]1[O:8][C:7]([C:9]2[C:13]([CH:14]=O)=[CH:12][N:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH3:22]>[O-2].[O-2].[Mn+4].C1(C)C=CC=CC=1>[N+:1]([C:4]1[O:8][C:7]([C:9]2[C:13]([C:14]#[N:22])=[CH:12][N:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 203262553-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 203261583-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbonitrile

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

Boil (under reflux) 5 g of 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carboxaldehyde together with 7.6 g of activated manganese dioxide and 300 ml of toluene with the introduction of ammonia using a water-trap. Filter after 5 hours and then evaporate the filtrate to dryness in vacuo before recrystallizing three times from dimethylformamide and water to obtain 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carbonitrile [m.p. 190° to 192° C].

Workup

  1. filtrationFilter after 5 hours
  2. customevaporate the filtrate to dryness in vacuo
  3. custombefore recrystallizing three times from dimethylformamide and water

Sources & evidence

ORD record
ord-5f6599fe25394fb79b76e3ec59868c49
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Reaction notes

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