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

HRID 873812Notes

Reaction equation

HRID 873812 reaction equation
[F: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>[F: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 1785268393-Fluoro-5-nitropyridin-2-OL

Product 1

HCID 1177029793-fluoro-1-methyl-5-nitropyridin-2(1H)-oneYield 93.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 3-fluoro-2-hydroxy-5-nitropyridine (2.03 g, 12.84 mmol) and K2CO3 (3.55 g, 25.7 mmol) in DMF (20 mL) under Ar was added MeI (1.20 mL, 19.26 mmol). The reaction mixture was stirred for 1 hr at rt, concentrated, diluted with water (100 mL), and extracted with CH2Cl2. (2×150 mL) The combined organic layers were washed with water, dried over Na2SO4 and evaporated to afford the crude title product (2.06 g, 11.97 mmol, 93% yield) as a yellow solid. tR: 2.22 min (HPLC 1); tR: 0.49 min (LC-MS 2); ESI-MS: 173 [M+H]+ (LC-MS 2).

Workup

  1. concentrationconcentrated
  2. additiondiluted with water (100 mL)
  3. extractionextracted with CH2Cl2
  4. wash(2×150 mL) The combined organic layers were washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-6f5fdc38d2f547a18688ee132b12dfb3
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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