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

HRID 15302

반응식

HRID 15302 반응식
[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[N:13]=2)[N:8]=[CH:7][C:6]=1[Cl:17].[C:19](=O)([O-])[O-].[K+].[K+].C=O.C(OCC)(=O)C>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1CCCCC1.O>[Cl:17][C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:5]=1[C:4](=[CH2:19])[C:3]([O:2][CH3:1])=[O:18])=[N:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=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

A mixture of methyl[3-chloro-6-(methyloxy)-1,5-naphthyridin-4-yl]acetate (43.3 g, 162 mmol), benzyltriethylammonium chloride (71.2 g, 313 mmol), potassium carbonate (42 g, 304 mmol) and paraformaldehyde (42 g) in cyclohexane (1060 ml) was heated at 80° C. for 24 h, cooled and treated with ethyl acetate and water. After separation, the aqueous was extracted with ethyl acetate. The combined organic phases were dried and the solvent was removed. The residue was subjected to column chromatography on silica gel using hexane/15% ethyl acetate to provide the desired compound (40.2 g, 89%).

후처리

  1. temperaturecooled
  2. customAfter separation
  3. extractionthe aqueous was extracted with ethyl acetate
  4. customThe combined organic phases were dried
  5. customthe solvent was removed

출처 및 근거

ORD 기록
ord-8a5f8952a0f6427990cce09d7e945dcd
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732461B2

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