Water → 2-Methyl-3-nitro-6-(1H-1,2,4-triazol-1-yl)pyridine

HRID 1931572Notes

Reaction equation

HRID 1931572 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH3:11])[N:3]=1.[NH:12]1[CH:16]=[N:15][CH:14]=[N:13]1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH3:11][C:4]1[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=[C:2]([N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 247280146-Bromo-2-methyl-3-nitropyridine

Product 1

HCID 579651682-Methyl-3-nitro-6-(1H-1,2,4-triazol-1-yl)pyridineYield 71%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 2-bromo-6-methyl-5-nitropyridine (ECA International Corporation, Palatine, Ill., USA; 2 g, 9.2 mmol), 1,2,4-triazole (Aldrich Chemical Company, Inc., Milwaukee, Wis., USA 0.64 g, 9.2 mmol) and potassium carbonate (1.27 g, 9.2 mmol) in dimethylsulfoxide (4 mL) was stirred at room temperature for 1.5 days and then poured into a mixture of ice and water (400 mL). The resulting mixture was stirred until all of the ice melted to give a dark purple slurry. The solid was filtered off to give 2-methyl-3-nitro-6-[1,2,4]triazol-1-yl-pyridine (1.34 g, 71%) as a purple solid with a purity estimated at 93% by LC-MS. This was used directly in the next step without further purification.

Workup

  1. customto give a dark purple slurry
  2. filtrationThe solid was filtered off

Sources & evidence

ORD record
ord-be10d49e31754e658bd23079a5bb429e
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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