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

HRID 839196Notes

Reaction equation

HRID 839196 reaction equation
N.C1O[CH:5]([C:6]2[C:7]([C:15]3[O:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=3)=[N:8][N:9](C(OC)=O)[CH:10]=2)[O:4]C1.Cl>O1CCOCC1.O>[N+:20]([C:17]1[O:16][C:15]([C:7]2[C:6]([CH:5]=[O:4])=[CH:10][NH:9][N:8]=2)=[CH:19][CH:18]=1)([O-:22])=[O:21]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 203260461-Methoxycarbonyl-3-(5-nitro-2-furyl)pyrazole-4-carboxaldehyde-ethyleneacetal

Product 1

HCID 1785198815-(5-nitrofuran-2-yl)-1H-pyrazole-4-carbaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Add 54 ml of concentrated ammonia solution dropwise to a suspension of 95.5 g of 1-methoxycarbonyl-3-(5-nitro-2-furyl)pyrazole-4-carboxaldehyde-ethyleneacetal in 750 ml of dioxan. Stir the resulting admixture for 12 minutes. Then add thereto 160 ml of 2N hydrochloric acid to adjust its pH to 1. Stir the thus-acidified product for 30 minutes before diluting it with 2000 ml of water. Allow the resulting precipitate to stand overnight in a cooling cupboard to obtain a quantitative yield of 3-(5-nitro-2-furyl)-1H-pyrazole-4-carboxaldehyde with a melting point of 184° to 186° C.

Workup

  1. additionThen add
  2. stirringStir the thus-acidified product for 30 minutes
  3. waitto stand overnight in a cooling cupboard

Sources & evidence

ORD record
ord-8025b66caf8e437b91607d36afee1a6d
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Reaction notes

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