Dimethyl Sulfate → 1-methyl-4-nitro-1H-pyrazole

HRID 450161

Reaction equation

HRID 450161 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].S(OC)(O[CH3:13])(=O)=O>[OH-].[Na+]>[CH3:13][N:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]1

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 163764-nitro-1H-pyrazole

Product 1

HCID 198951-methyl-4-nitro-1H-pyrazoleYield 50%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 0.996 g (8.82 mmol) of 4-nitropyrazole (J. Med. Chem. 2005, 48, 5780-5793) and 1.33 g (10.6 mmol) of dimethyl sulphate in 10 mL of 1 M NaOH was heated at 35° C. for 48 hrs. The reaction mixture was cooled to RT and the precipitate was filtered, washed with water, and dried to give 0.561 g (50% yield) of 1-methyl-4-nitro-1H-pyrazole: 1H NMR (DMSO-d6) δ8.83 (s, 1H), 8.22 (s, 1H), 3.91 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. filtrationthe precipitate was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-2cd3f5054be74df787f10281c223a1cd
Source dataset
uspto-grants-2013_07
Patent number
US08486939B2

Linked notes

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