Formaldehyde → Methyl 2-[3-chloro-6-(methoxy)-1,5-naphthyridin-4-yl]-2-propenoate

HRID 15124

반응식

HRID 15124 반응식
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH2:12][C:13]([O:15][CH3:16])=[O:14])=[N:9][C:8]([O:17][CH3:18])=[CH:7][CH:6]=2.[C:19](=O)([O-])[O-].[K+].[K+].C=O.C(OCC)(=O)C>C1CCCCC1.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12](=[CH2:19])[C:13]([O:15][CH3:16])=[O:14])=[N:9][C:8]([O:17][CH3:18])=[CH:7][CH:6]=2

참가 물질

8

반응물 4

HCID 712FormaldehydeHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 57707490Methyl [3-chloro-6-(methyloxy)-[1,5]naphthyridin-4-yl]acetate

생성물 1

HCID 57486868Methyl 2-[3-chloro-6-(methoxy)-1,5-naphthyridin-4-yl]-2-propenoate수율 89%

시약·촉매·용매 3

HCID 66133Benzyl triethylammonium chloride촉매HCID 962Water용매HCID 8078Cyclohexane용매

반응 조건

온도
80 °C

실험 절차

To a solution of methyl [3-chloro-6-(methyloxy)-1,5-naphthyridin-4-yl]acetate (43 g, 162 mmol) in cyclohexane (1060 ml) was added benzyltriethylammonium chloride (71.2 g, 313 mmol), potassium carbonate (42 g, 304 mmol) and paraformaldehyde (42 g). The reaction mixture was then heated at 80° C. for 24 hours, cooled and treated with ethyl acetate and water. The aqueous was extracted with ethyl acetate. The combined organic phases were dried and the solvent was removed under reduced pressure. The residue was subjected to column chromatography on silica gel using a hexane and ethyl acetate gradient to provide the desired compound (40 g, 89%).

후처리

  1. temperaturecooled
  2. extractionThe aqueous was extracted with ethyl acetate
  3. customThe combined organic phases were dried
  4. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-6b4e56ec1d8f4d4cac9a4ee473daecdc
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732460B2

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