Sodium Bicarbonate → 2,7-Dimethoxy-1,5-naphthyridine

HRID 656876Notes

Reaction equation

HRID 656876 reaction equation
Br[C:2]1[C:3]([O:14][CH3:15])=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[C:9]([O:12][CH3:13])[CH:8]=[CH:7]2.C(=O)([O-])O.[Na+].[H][H]>CO.[Pd]>[CH3:13][O:12][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[CH:2][C:3]([O:14][CH3:15])=[CH:4][N:5]=2)[N:10]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 585793648-Bromo-2,7-dimethoxy-1,5-naphthyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 585794032,7-Dimethoxy-1,5-naphthyridineYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

8-Bromo-2,7-bis(methoxy)-1,5-naphthyridine (11.21 g, 41.673 mmol) was stirred in MeOH (400 mL) with sodium hydrogen carbonate (7.00 g, 83.35 mmol) and 10% palladium on carbon (2.8 g), and the resulting suspension was hydrogenated at 1 atmosphere of hydrogen pressure for 18 h. The mixture was filtered with suction through celite and the solids were washed with ethanol (300 ml). The filtrate was concentrated under reduced pressure and the residue treated with DCM (300 ml) and water (300 ml). The aqueous phase was extracted with DCM (2×300 ml). The combined organic phases were separated, dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure to give 2,7-bis(methoxy)-1,5-naphthyridine as a cream solid (7.45 g, 94%).

Workup

  1. filtrationThe mixture was filtered with suction through celite
  2. washthe solids were washed with ethanol (300 ml)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionthe residue treated with DCM (300 ml) and water (300 ml)
  5. extractionThe aqueous phase was extracted with DCM (2×300 ml)
  6. customThe combined organic phases were separated
  7. dry with materialdried over anhydrous magnesium sulphate
  8. filtrationfiltered
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8a233f64e8ec470896436e56b69f4f34
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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