Nitric Acid → 5-Chloro-3-methyl-4-nitro-1-phenyl-1H-pyrazole

HRID 1580116Notes

Reaction equation

HRID 1580116 reaction equation
[Cl:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[N+:14]([O-])([O:16]C(=O)C)=[O:15].[N+]([O-])(O)=O>C(OC(=O)C)(=O)C>[Cl:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([CH3:13])[C:3]=1[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 11557Acetyl nitrateHCID 27357715-Chloro-3-methyl-1-phenyl-1H-pyrazole

Product 1

HCID 8493605-Chloro-3-methyl-4-nitro-1-phenyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent2×

Procedure

A solution of 9.6 g (0.05 mole) of 5-chloro-3-methyl-1-phenylpyrazole and 25 ml of acetic anhydride was added at 10°C to a solution of acetyl nitrate prepared from 25 ml of 90% nitric acid and 10 ml of acetic anhydride. The solution was stirred 2 hours at 20°-30°C and carefully poured onto ice water. The solid was filtered off and washed with cold water. One recrystallization from ethanol gave long white needles of product.

Workup

  1. additioncarefully poured onto ice water
  2. filtrationThe solid was filtered off
  3. washwashed with cold water
  4. customOne recrystallization from ethanol
  5. customgave long white needles of product

Sources & evidence

ORD record
ord-842f706eb2ed472ea0a5c413e714db82
Source dataset
uspto-grants-1976_01
Patent number
US03932453

Reaction notes

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