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

HRID 15302

Reaction equation

[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

Participants

Conditions

Temperature: 80 °C

Procedure

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%).

Workup

temperaturecooled
customAfter separation
extractionthe aqueous was extracted with ethyl acetate
customThe combined organic phases were dried
customthe solvent was removed

Sources & evidence

ORD record: ord-8a5f8952a0f6427990cce09d7e945dcd
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732461B2

Linked notes

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