Iodoethane → 1-Ethyl-4-hydroxy-3-nitropyridin-2(1H)-one

HRID 1376215Notes

Reaction equation

HRID 1376215 reaction equation
[N+:1]([C:4]1[C:5]([OH:11])=[N:6][CH:7]=[CH:8][C:9]=1[OH:10])([O-:3])=[O:2].[H-].[Na+].[CH2:14](I)[CH3:15]>CN(C=O)C>[CH2:14]([N:6]1[CH:7]=[CH:8][C:9]([OH:10])=[C:4]([N+:1]([O-:3])=[O:2])[C:5]1=[O:11])[CH3:15]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 178526878HCID 178526878, compound

Product 1

HCID 714223361-Ethyl-4-hydroxy-3-nitropyridin-2(1H)-oneYield 53.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-nitro-pyridine-2,4-diol (1.0 g, 6.41 mmol) in DMF (10 mL) at 0° C., was added NaH (0.51 g, 12.82 mmol 60% in mineral oil). After stirring at 0° C. for 15 min, ethyl iodide (1.10 g, 7.05 mmol) was added and the reaction was stirred at 55° C. for 17 h. After cooling to room temperature, the mixture was poured into ice water, and then filtered to remove insoluble material. The filtrate was acidified with 1 N HCl, extracted with CH2Cl2, dried with MgSO4, and concentrated. The product was rinsed with EtOH to give 1-ethyl-4-hydroxy-3-nitro-1H-pyridin-2-one (0.63 g, 53% yield). 1H-NMR (DMSO): δ, 7.79 (d, 1H, J=7.6 Hz), 6.09 (d, 1H, J=7.6 Hz), 3.90 (q, 2H, J=7.2 Hz), 1.19 (t, 3H, J=7.2 Hz).

Workup

  1. stirringthe reaction was stirred at 55° C. for 17 h
  2. temperatureAfter cooling to room temperature
  3. filtrationfiltered
  4. customto remove insoluble material
  5. extractionextracted with CH2Cl2
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated
  8. washThe product was rinsed with EtOH

Sources & evidence

ORD record
ord-92290da4324848c1914dea029263f8cd
Source dataset
uspto-grants-2007_01
Patent number
US07169926B1

Reaction notes

Loading…