Dimethylformamide → 1,3-dimethyl-5-nitropyridin-2(1H)-one

HRID 469840Notes

Reaction equation

HRID 469840 reaction equation
ON1C=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4](C)[CH2:3]1.[H-].[Na+].CI.[CH3:16][N:17]([CH:19]=[O:20])[CH3:18]>>[CH3:16][N:17]1[CH:18]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([CH3:3])[C:19]1=[O:20]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 674578381-Hydroxy-3-methyl-5-nitropyridine

Product 1

HCID 46575261,3-dimethyl-5-nitropyridin-2(1H)-one

Procedure

A mixture of 1 g (6.49 mmol) 1-hydroxy-3-methyl-5-nitropyridine, 0.197 g (7.8 mmol) NaH and 0.61 ml (9.73 mmol) MeI in 20 ml DMF is stirred at room temperature for 20 h. Then the reaction mixture is poured on water and extracted 3× with EtOAc. The combined organic layers are washed with water and saturated NaCl solution, dried over MgSO4, filtered and the filtrate is concentrated in vacuo to afford the title compound as off-white crystals.

Workup

  1. additionThen the reaction mixture is poured on water
  2. extractionextracted 3× with EtOAc
  3. washThe combined organic layers are washed with water and saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-a0a2de63eef8454381f57c8dc7026196
Source dataset
uspto-grants-2014_01
Patent number
US08629168B2

Reaction notes

Loading…