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

HRID 873799Notes

Reaction equation

HRID 873799 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)-oneYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 3-chloro-2-hydroxy-5-nitropyridine (10 g, 57.3 mmol) and K2CO3 (15.84 g, 115 mmol) in DMF (100 mL) under Ar was added MeI (5.37 mL, 86 mmol) at 0° C. The reaction mixture was stirred for 1 hr at rt, concentrated, diluted with water, and extracted with EtOAc. The combined organic layers were washed with water, dried over Na2SO4, and evaporated to afford the title product (10.38 g, 55.0 mmol, 96% yield) as a yellow solid. tR: 2.90 min (HPLC 1).

Workup

  1. concentrationconcentrated
  2. additiondiluted with water
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-7df3e46ab469405eba3a757eddd74bb2
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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