Sodium Methoxide → 2-Chloro-7,8-dihydro-1,6-naphthyridin-5(6H)-one

HRID 2277600Notes

Reaction equation

HRID 2277600 reaction equation
COC([N:5]1[CH2:14][CH2:13][C:12]2[N:11]=[C:10]([Cl:15])[CH:9]=[CH:8][C:7]=2[C:6]1=[O:16])=O.C[O-].[Na+]>O1CCOCC1>[Cl:15][C:10]1[CH:9]=[CH:8][C:7]2[C:6](=[O:16])[NH:5][CH2:14][CH2:13][C:12]=2[N:11]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 58155423Methyl 2-chloro-5-oxo-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

Product 1

HCID 722129652-Chloro-7,8-dihydro-1,6-naphthyridin-5(6H)-oneYield 63%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-chloro-5-oxo-7,8-dihydro-5H-[1,6]naphthyridine-6-carboxylic acid methyl ester (60 mg, 0.25 mmol) and sodium methoxide (40 mg, 0.75 mmol) in 2 mL of 1,4-dioxane was subject to microwave reaction at 110° C. for 30 min. After removal of 1,4-dioxane, the residue was dissolved in DCM and the DCM solution was washed with water and brine. The organic layer was then dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product. Prep-TLC separation (30% EtOAc in hexane) then afforded the tile compound (28 mg, 63%) as a white solid. MS: 183.1 (M+H+).

Workup

  1. customreaction at 110° C. for 30 min
  2. customAfter removal of 1,4-dioxane
  3. dissolutionthe residue was dissolved in DCM
  4. washthe DCM solution was washed with water and brine
  5. customThe organic layer was then dried over anhy
  6. filtrationNa2SO4, filtered
  7. concentrationconcentrated in vacuo
  8. customto give a crude product
  9. customPrep-TLC separation (30% EtOAc in hexane)

Sources & evidence

ORD record
ord-5cf99a5986bf47bcb6985c84daa9dee6
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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