Hydrazine → 5-Hydrazino-1,3-dimethyl-4-nitro-1H-pyrazole

HRID 1678847Notes

Reaction equation

HRID 1678847 reaction equation
[NH2:1][NH2:2].[CH3:3][N:4]1[C:8](Cl)=[C:7]([N+:10]([O-:12])=[O:11])[C:6]([CH3:13])=[N:5]1>C(O)CC>[NH:1]([C:8]1[N:4]([CH3:3])[N:5]=[C:6]([CH3:13])[C:7]=1[N+:10]([O-:12])=[O:11])[NH2:2]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 2795155-Chloro-1,3-dimethyl-4-nitro-1H-pyrazole

Product 1

HCID 35372575-Hydrazino-1,3-dimethyl-4-nitro-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent2×

Procedure

39 gms. of hydrazine are dissolved in 500 ml. of n-propanol and 105 gms. of 1,3-dimethyl-4-nitro-5-chloro-1H-pyrazole dissolved in propanol are added dropwise at 100°. The reaction mixture is then refluxed for 4 hours. On cooling, 5-hydrazino-1,3-dimethyl-4-nitro-1H-pyrazole crystallizes in the form of yellow needles. By concentrating the mother liquor an additional quantity of product is obtained. The combined crude is recrystallized from propanol, yield 98 gms. of yellow needles, m.p. 177°-179°.

Workup

  1. additionare added dropwise at 100°
  2. temperatureThe reaction mixture is then refluxed for 4 hours
  3. temperatureOn cooling
  4. custom5-hydrazino-1,3-dimethyl-4-nitro-1H-pyrazole crystallizes in the form of yellow needles
  5. concentrationBy concentrating the mother liquor an additional quantity of product
  6. customis obtained
  7. customis recrystallized from propanol, yield 98 gms

Sources & evidence

ORD record
ord-a5f54b3418a24a558bb2d94e0e192dd0
Source dataset
uspto-grants-1978_03
Patent number
US04077956

Reaction notes

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