Diethyl Ether → 1,5-Dimethyl-3-nitropyridin-2-one

HRID 869084Notes

Reaction equation

HRID 869084 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH3:11])=[CH:4][N:3]=1.[C:12]([O-])([O-])=O.[K+].[K+].CI.CCOCC>CN(C=O)C>[CH3:12][N:3]1[CH:4]=[C:5]([CH3:11])[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]1=[O:1]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178430719HCID 178430719, compound

Product 1

HCID 51067591,5-Dimethyl-3-nitropyridin-2-oneYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 10 g (63.6 mmol) 2-hydroxy-5-methyl-3-nitropyridine and 17.58 g (127 mmol) K2CO3 in 100 ml DMF, 5.96 ml (95 mmol) MeI was added at 0° C. Afterwards the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated, diluted with water and extracted three times with CH2Cl2. The organic layers were combined, dried over Na2SO4, filtered and concentrated to obtain an orange slurry. The residue was treated with ether and the precipitate was filtered off and dried under high vacuum to obtain 9.74 g (57.9 mmol, 91% yield) of the title compound as an orange solid. LCMS: (M+H)=169; tR=0.47 min (LC-MS 6). HPLC: tR=1.70 min (HPLC 8). 1H-NMR (DMSO-d6, 400 MHz) δ ppm 8.30 (d, 1H) 8.08 (m, 1H) 3.50 (s, 3H) 2.09 (s, 3H).

Workup

  1. additionwas added at 0° C
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with water
  4. extractionextracted three times with CH2Cl2
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto obtain an orange slurry
  9. filtrationthe precipitate was filtered off
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-b2917b69b8fe4fa88f6b4d16bbd8bf15
Source dataset
uspto-grants-2015_03
Patent number
US08969341B2

Reaction notes

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