Methyl iodide → 3-chloro-1-methyl-5-nitropyridin-2(1H)-one

HRID 2204304Notes

Reaction equation

HRID 2204304 reaction equation
[Cl:1][C:2]1[C:3]([OH:11])=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[C:12]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[Cl:1][C:2]1[C:3](=[O:11])[N:4]([CH3:12])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178526838HCID 178526838, compound

Product 1

HCID 867031063-chloro-1-methyl-5-nitropyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-chloro-2-hydroxy-5-nitropyridine [22353-38-4] (143 mmol) and K2CO3 (286 mmol) in DMF (250 mL) was added methyl iodide (215 mmol) at 0° C. and the reaction mixture was stirred at rt for 3 h. The reaction mixture was concentrated, diluted with H2O and extracted with EtOAc (2×). The combined organic layers were washed with H2O, dried (Na2SO4) and concentrated to afford the title compound as a yellow solid. tR: 2.90 min (HPLC 3); ESI-MS: tR=0.63 min, [M+H]+189/191 (LC-MS 1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with H2O
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic layers were washed with H2O
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-07d70cd416284689b22149a1bd230695
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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