Sodium Carbonate → Methyl 4-{1-[2-(dimethylamino)ethyl]-2-oxo-1,2-dihydropyridin-3-yl}benzoate

HRID 910615Notes

Reaction equation

HRID 910615 reaction equation
[O:1]=[C:2]1[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=2)=[CH:6][CH:5]=[CH:4][NH:3]1.C(=O)([O-])[O-].[Na+].[Na+].Cl.Cl[CH2:26][CH2:27][N:28]([CH3:30])[CH3:29].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:29][N:28]([CH3:30])[CH2:27][CH2:26][N:3]1[CH:4]=[CH:5][CH:6]=[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=2)[C:2]1=[O:1]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 53217923Methyl 4-(2-oxo-1,2-dihydropyridin-3-yl)benzoate

Product 1

HCID 57584036Methyl 4-{1-[2-(dimethylamino)ethyl]-2-oxo-1,2-dihydropyridin-3-yl}benzoateYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 4-(2-oxo-1,2-dihydropyridin-3-yl)benzoate (1.04 g) was dissolved in N,N-dimethylformamide (20 mL), and sodium carbonate (1.88 g) and (2-chloroethyl)dimethylamine hydrochloride (981 mg) were added, followed by stirring at 80° C. for 7 hours. Then, potassium carbonate (628 mg) was added, followed by stirring for 2 hours. The reaction mixture was concentrated under reduced pressure, water was added to the residue, followed by extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by NH-silica gel column chromatography (hexane:ethyl acetate=9:1 to 1:1) to obtain methyl 4-{1-[2-(dimethylamino)ethyl]-2-oxo-1,2-dihydropyridin-3-yl}benzoate (954 mg) as a yellow oil.

Workup

  1. stirringby stirring for 2 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure, water
  3. additionwas added to the residue
  4. extractionfollowed by extraction with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe resulting residue was purified by NH-silica gel column chromatography (hexane:ethyl acetate=9:1 to 1:1)

Sources & evidence

ORD record
ord-1742909c00f74392bf6f34ddc20188af
Source dataset
uspto-grants-2011_09
Patent number
US08022208B2

Reaction notes

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