Methyl iodide → Methyl 1-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate

HRID 2400218Notes

Reaction equation

HRID 2400218 reaction equation
[O:1]=[C:2]1[NH:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][CH:4]=[CH:3]1.[C:12](=O)([O-])[O-].[K+].[K+].CI>CS(C)=O>[CH3:12][N:7]1[C:2](=[O:1])[CH:3]=[CH:4][CH:5]=[C:6]1[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 12342664Methyl 6-oxo-1,6-dihydropyridine-2-carboxylate

Product 1

HCID 12342666Methyl 1-methyl-6-oxo-1,6-dihydropyridine-2-carboxylateYield 28.52%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In Example 22, 0.4006 g (2.611 mmol) of methyl 6-oxo-1,6-dihydropyridine-2-carboxylate and 0.4006 g (2.899 mmol) of potassium carbonate were combined in a 25 mL RBF. 1 mL of DMSO followed by 4 mL (64.25 mmol) of methyl iodide was added and the reaction refluxed for 4 hours. The solvent was removed under reduced pressure and the resulting oil was extracted with hot hexanes (8×25 mL), the extracts were combined and solvent removed to yield a yellow oil. Recrystallization from hexanes yielded the product as white/yellow crystals (0.1245 g, 28.52%). Melting Point: 56-57° C. IR: (Nujol) 3437.61, 1731.13, 1652.94, 1590.77, 1457.45, 1443.48, 1379.43, 1265.53, 1218.08, 1156.78, 1086.06, 900.89, 825.45, 817.06, 765.03, 755.48, 722.85 cm−1. 1H NMR: (500 MHz, CDCl3) 3.67 (s, 3H), 3.91 (s, 3H), 6.71 (dd, J=1.2, 9.1 Hz, 1H), 6.74 (dd, J=1.2, 6.8 Hz, 1H), 7.29 (dd, J=6.7, 9.1 Hz, 1H). 13C NMR: (126 MHz, CDCl3) 33.40, 52.90, 110.42, 124.46, 137.21, 138.21, 162.45, 162.70.

Workup

  1. additionwas added
  2. temperaturethe reaction refluxed for 4 hours
  3. customThe solvent was removed under reduced pressure
  4. extractionthe resulting oil was extracted with hot hexanes (8×25 mL)
  5. customsolvent removed
  6. customto yield a yellow oil
  7. customRecrystallization from hexanes

Sources & evidence

ORD record
ord-51b99759acbe47d5ac659a4c0535d0fb
Source dataset
uspto-grants-2014_08
Patent number
US08795630B2

Reaction notes

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