Methyl iodide → 2,7-Dimethoxy-1,5-naphthyridine

HRID 2279317Notes

Reaction equation

HRID 2279317 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[N:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13](O)=[CH:12]2.IC.C(OCC)(=O)C>CC(C)=O>[CH3:7][O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][C:13]([O:4][CH3:1])=[CH:14][N:15]=2)[N:10]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 1363794146-Methoxy-[1,5]naphthyridin-3-ol

Product 1

HCID 585794032,7-Dimethoxy-1,5-naphthyridineYield 54.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (13.84 g, 100.1 mmol, 2.0 eq) is added at room temperature to a stirred solution of 6-methoxy-[1,5]naphthyridin-3-ol (9.8 g, 50.06 mmol, 1.0 eq) in acetone (300 mL), followed by iodomethane (3.74 mL, 60.1 mmol, 1.2 eq). After 4 hours stirring under reflux conditions, the solid is removed by filtration and the filtrate is concentrated to give a residue that is extracted with ethyl acetate (3×100 mL) and water (100 mL). The combined organic layers are washed with brine, dried over sodium sulfate, filtered and concentrated to give a residue that is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 6:1, v/v) to afford 2,7-dimethoxy-[1,5]naphthyridine as a yellow solid (5.2 g, 52% yield).

Workup

  1. customthe solid is removed by filtration
  2. concentrationthe filtrate is concentrated
  3. customto give a residue that
  4. extractionis extracted with ethyl acetate (3×100 mL) and water (100 mL)
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a residue that
  10. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-0dfde166b77b4aa786ea6d3156000203
Source dataset
uspto-grants-2015_09
Patent number
US09133219B2

Reaction notes

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