Water → Methyl [3-chloro-6-(methyloxy)-[1,5]naphthyridin-4-yl]acetate
Reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH:12](C(OC)=O)[C:13]([O:15][CH3:16])=[O:14])=[N:9][C:8]([O:21][CH3:22])=[CH:7][CH:6]=2.[Cl-].[Li+].O.C(OCC)(=O)C>CS(C)=O>[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:21][CH3:22])=[CH:7][CH:6]=2Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of dimethyl [3-chloro-6-(methyloxy)-1,5-naphthyridin-4-yl]propanedioate (56 g, 173 mmol) in dimethylsulfoxide (1210 ml) was added lithium chloride (14.9 g, 350 mmol) and water (3.2 ml, 180 mmol). The mixture was heated to 100° C. for 16 hours then cooled and treated with ethyl acetate and water. The organic phase was washed twice with water, the aqueous extracted with ethyl acetate and this water-washed. 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 (43 g, 94%).
Workup
- temperaturethen cooled
- washThe organic phase was washed twice with water
- extractionthe aqueous extracted with ethyl acetate
- washthis water-washed
- customThe combined organic phases were dried
- customthe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-a1419524ecf446e093454396f5698dbf
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07732460B2
Reaction notes
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