Nitric Acid → 1-Methyl-5-(5-nitrofuran-2-yl)-1H-pyrazole-4-carbonitrile

HRID 839249Notes

Reaction equation

HRID 839249 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([CH3:11])[N:9]=[CH:8][C:7]=1[C:12]#[N:13].S(=O)(=O)(O)O.[N+:19]([O-])([OH:21])=[O:20]>O>[CH3:11][N:10]1[C:6]([C:2]2[O:1][C:5]([N+:19]([O-:21])=[O:20])=[CH:4][CH:3]=2)=[C:7]([C:12]#[N:13])[CH:8]=[N:9]1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 20326245HCID 20326245, compound

Product 1

HCID 203260631-Methyl-5-(5-nitrofuran-2-yl)-1H-pyrazole-4-carbonitrileYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add 1.0 g of 5-(2-furyl)-1-methylpyrazole-4-carbonitrile to 4.1 ml of concentrated sulfuric acid at from -10° C to -12° C and, at the same temperature, slowly add a nitrating mixture (0.91 ml of concentrated sulfuric acid and 0.45 ml of fuming nitric acid) dropwise to the resulting reaction mixture for 1 hour at this temperature, and then pour the prepared solution onto 20 g of ice and water. Crystallize the thus-prepared precipitate in an ice-bath to obtain an 80% yield of 1-methyl-5-(5-nitro-2-furyl)pyrazole-4-carbonitrile [m.p. 149.5° to 151.5° C].

Workup

  1. customdropwise to the resulting reaction mixture for 1 hour at this temperature
  2. customCrystallize the thus-prepared precipitate in an ice-bath

Sources & evidence

ORD record
ord-97ae6c3f16164fe5ae115e8007b9ffe5
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Reaction notes

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