Nitric Acid → 3-chloro-1-Methyl-4-nitro-1H-pyrazole

HRID 445541Notes

Reaction equation

HRID 445541 reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][N:4]([CH3:7])[N:3]=1.[N+:8]([O-])([OH:10])=[O:9]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:6]([N+:8]([O-:10])=[O:9])=[CH:5][N:4]([CH3:7])[N:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 136300863-Chloro-1-methyl-1H-pyrazole

Product 1

HCID 596200183-chloro-1-Methyl-4-nitro-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 3-chloro-1-methylpyrazole (Maybridge, Basel, Switzerland, 953 mg, 8.18 mmol) in concentrated sulfuric acid (1.4 ml), cooled with an ice-bath, was added over 30 min fuming nitric acid (1.19 mL, 28.6 mmol). The reaction mixture was stirred at rt for 2 h before being poured on ice/water and extracted with EtOAc (2×). The organic layers were washed with saturated aqueous NaHCO3 (2×) and brine, dried over Na2SO4, filtered, evaporated and dried over vacuum to give the title compound as a white solid (HPLC tR 2.24 min (Method A); M+H=162 MS-ES)

Workup

  1. additionbefore being poured on ice/water
  2. extractionextracted with EtOAc (2×)
  3. washThe organic layers were washed with saturated aqueous NaHCO3 (2×) and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customdried over vacuum

Sources & evidence

ORD record
ord-892208aa09c144218022f13a11eccf54
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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