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

HRID 15302

Reaktionsgleichung

Reaktionsgleichung von HRID 15302
[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

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 962WaterLösungsmittelHCID 8078CyclohexaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8a5f8952a0f6427990cce09d7e945dcd
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732461B2

Verknüpfte Notizen

Wird geladen…