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

HRID 910615노트

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HRID 910615 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-1742909c00f74392bf6f34ddc20188af
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022208B2

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