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

HRID 15124

Reaction equation

[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

Participants

Conditions

Temperature: 80 °C

Procedure

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%).

Workup

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

Sources & evidence

ORD record: ord-6b4e56ec1d8f4d4cac9a4ee473daecdc
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732460B2

Linked notes

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