Isoamyl Nitrite → 1H-Pyrazol-5-amine,1-methyl-4-nitro-(9CI)

HRID 1376877Notes

Reaction equation

HRID 1376877 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][CH:3]=1.[N:8]([O:10]CCC(C)C)=[O:9]>>[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

Participants

3

Reactant 2

HCID 8053Isoamyl NitriteHCID 1369272-Methyl-2H-pyrazol-3-ylamine

Product 1

HCID 5883821H-Pyrazol-5-amine,1-methyl-4-nitro-(9CI)

Procedure

Total yields of up to 46 percent are obtained when the 5-amino-1-methylpyrazole is converted with isoamyl nitrite to produce 5-amino-1-methyl-4-nitropyrazole and reduced with zinc(II)chloride to give 4,5-diamino-1-methylpyrazole according to H. Dorn, et al., Liebigs Ann. Chem. 717, p. 118 (1968).

Workup

  1. customTotal yields of up to 46 percent

Sources & evidence

ORD record
ord-7210d6ee4bb14b728aa00fa361390187
Source dataset
uspto-grants-1997_09
Patent number
US05663366

Reaction notes

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