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

HRID 1042769Notes

Reaction equation

HRID 1042769 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 RT, filtered through Celite, and washed with hot MeOH. 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 MeOH
  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-47830145e1624e018091b6550beca0a5
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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