Chloroform → 1-methyl-5-nitro-3-(2H-1,2,3-triazol-2-yl)pyridin-2(1H)-one

HRID 2406739Notes

Reaction equation

HRID 2406739 reaction equation
CI.[CH:3](Cl)(Cl)Cl.[N+:7]([C:10]1[CH:11]=[C:12]([N:17]2[N:21]=[CH:20][CH:19]=[N:18]2)[C:13]([OH:16])=[N:14][CH:15]=1)([O-:9])=[O:8].[N+:22]([C:25]1[CH:26]=[C:27]([N:32]2[CH:36]=[CH:35][N:34]=[N:33]2)[C:28]([OH:31])=[N:29][CH:30]=1)([O-:24])=[O:23]>C(=O)([O-])[O-].[Ag+2].O>[CH3:25][N:14]1[CH:15]=[C:10]([N+:7]([O-:9])=[O:8])[CH:11]=[C:12]([N:17]2[N:21]=[CH:20][CH:19]=[N:18]2)[C:13]1=[O:16].[CH3:3][N:29]1[CH:30]=[C:25]([N+:22]([O-:24])=[O:23])[CH:26]=[C:27]([N:32]2[CH:36]=[CH:35][N:34]=[N:33]2)[C:28]1=[O:31]

Participants

8

Reactant 4

HCID 6212ChloroformHCID 6328Methyl iodideHCID 1785268425-nitro-3-(1H-1,2,3-triazol-1-yl)pyridin-2-olHCID 178526843HCID 178526843, compound

Product 2

HCID 866838671-methyl-5-nitro-3-(2H-1,2,3-triazol-2-yl)pyridin-2(1H)-oneHCID 866838681-methyl-5-nitro-3-(1H-1,2,3-triazol-1-yl)pyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 962WaterSolvent

Procedure

Silver carbonate (377 mg) and methyl iodide (366 W) were added to a chloroform (10 ml) solution containing the mixture of 5-nitro-3-(2H-1,2,3-triazol-2-yl)pyridin-2-ol and 5-nitro-3-(1H-1,2,3-triazol-1-yl)pyridin-2-ol (184 mg) obtained in the 1st step while shielding light, followed by reflux for 2 hours. Water was added, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=2:5 to 2:3), and a white solid of 1-methyl-5-nitro-3-(2H-1,2,3-triazol-2-yl)pyridin-2(1H)-one (28.1 mg) and a white solid of 1-methyl-5-nitro-3-(1H-1,2,3-triazol-1-yl)pyridin-2(1H)-one (23.3 mg) were thus obtained.

Workup

  1. additioncontaining
  2. customobtained in the 1st step
  3. temperatureby reflux for 2 hours
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe resultant was washed with saturated saline
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationSubsequently, the solvent was distilled away under reduced pressure
  8. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=2:5 to 2:3)

Sources & evidence

ORD record
ord-f1475a3751e94bfa9b966ca47ae17530
Source dataset
uspto-grants-2014_08
Patent number
US08809371B2

Reaction notes

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