Methyl iodide → Methyl 1-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate

HRID 1676330Notes

Reaction equation

HRID 1676330 reaction equation
[H-].[Li+].[O:3]=[C:4]1[C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=[CH:6][NH:5]1.I[CH3:15]>CN(C=O)C.CCOC(C)=O>[CH3:15][N:5]1[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[C:4]1=[O:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 62714Lithium hydrideHCID 579028Methyl 2-oxo-1,2-dihydropyridine-3-carboxylate

Product 1

HCID 819366Methyl 1-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

LiH (10 mg, 1.3 mmol) was added to the solution of methyl 2-oxo-1,2-dihydropyridine-3-carboxylate (0.10 g, 0.65 mmol) in DMF (3 mL) at 0° C. After stirring for 30 minutes, iodomethane (0.08 mL, 1.30 mmol) was added to the reaction mixture at the temperature, and the reaction was warmed to room temperature. After stirring for 3 days, the reaction mixture was diluted with EtOAc, quenched with ice water, extracted with EtOAc, dried over MgSO4, and concentrated to give the desired product. 1H NMR (400 MHz, CDCl3) δ 8.17 (dd, 1H), 7.58 (dd, 1H), 6.27 (t, 1H), 3.91 (s, 3H), 3.61 (s, 3H).

Workup

  1. stirringAfter stirring for 3 days
  2. customquenched with ice water
  3. extractionextracted with EtOAc
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2453e16a5fe248908a8ee4c5500dd40f
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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