Ammonium formate → 7-Methoxy-1H-1,6-naphthyridin-4-one

HRID 219147Notes

Reaction equation

HRID 219147 reaction equation
Br[C:2]1[C:3]([O:13][CH3:14])=[N:4][CH:5]=[C:6]2[C:11]=1[NH:10][CH:9]=[CH:8][C:7]2=[O:12].C([O-])=O.[NH4+]>CO.[Pd]>[CH3:14][O:13][C:3]1[CH:2]=[C:11]2[C:6]([C:7](=[O:12])[CH:8]=[CH:9][NH:10]2)=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 673185318-Bromo-7-methoxy-1,6-naphthyridin-4(1H)-one

Product 1

HCID 534871227-Methoxy-1H-1,6-naphthyridin-4-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

8-Bromo-7-methoxy-1H-[1,6]naphthyridin-4-one (12 g, 33.5 mmol) was dissolved in anhydrous methanol (240 mL) and 10% Dry Pd/C (2.4 g) was added carefully in portions. This was followed by portionwise addition of ammonium formate (24 g) which caused an exotherm. The reaction mixture was heated to reflux for 1 h. The reaction mixture was cooled to room temperature, filtered through Celite, and washed with hot methanol. The filtrate was concentrated and the residue purified by column chromatography on silica gel (230-400 mesh) eluting with ethyl acetate-methanol.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 h
  3. filtrationfiltered through Celite
  4. washwashed with hot methanol
  5. concentrationThe filtrate was concentrated
  6. customthe residue purified by column chromatography on silica gel (230-400 mesh)
  7. washeluting with ethyl acetate-methanol

Sources & evidence

ORD record
ord-c90bd93ea5e04594a06b5ea96adb836b
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

Loading…