Methyl iodide → 5-Chloro-1-methyl-3-nitropyridin-2-one

HRID 2204314Notes

Reaction equation

HRID 2204314 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([N+:11]([O-:13])=[O:12])[C:7]([OH:10])=[N:8][CH:9]=1.[CH3:14]I>O>[Cl:3][C:4]1[CH:5]=[C:6]([N+:11]([O-:13])=[O:12])[C:7](=[O:10])[N:8]([CH3:14])[CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178526657HCID 178526657, compound

Product 1

HCID 867031195-Chloro-1-methyl-3-nitropyridin-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

NaH (52.6 mmol) was slowly added at 5° C. to a solution of 5-chloro-2-hydroxy-3-nitropyridine [21427-61-2] (43.8 mmol) and the mixture was stirred at 5° C. for 30 min. Methyl iodide (65.7 mmol) was added and the mixture was stirred at rt for 20 h. The mixture was diluted with H2O and extracted with EtOAc (3×). The combined organic phases were washed successively with H2O and brine, dried (Na2SO4), filtered and concentrated to afford the title compound. ESI-MS: tR=0.55 min, [M+H]+ 189/191 (LC-MS 1).

Workup

  1. stirringthe mixture was stirred at rt for 20 h
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic phases were washed successively with H2O and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6188df1b48ae4b4a8cc928f679b2d13f
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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