Reaction #1528435

Reaction equation

Ethyl (6-bromo-2-nitro-pyridin-3-yloxy)acetate

→

6-Bromo-4H-pyrido[3,2-b][1,4]oxazin-3-one

Solvents

AcOH

EtOAc

Conditions

Workup

1. 1
   Temperaturewas cooled to room temperature
2. 2
   FiltrationThe mixture was filtered through a pad of silica gel
3. 3
   Concentrationthe filtrate was concentrated in vacuo
4. 4
   Otherthe residue recrystallized from MeOH (15 g, 52%)

Procedure

Ethyl (6-bromo-2-nitro-pyridin-3-yloxy)acetate (38 g, 0.125 mole) was dissolved in glacial AcOH (150 mL), and iron powder (20 g, 0.36 mole) was added. The mixture was mechanically stirred and heated at 90° C. for 5 hr, then was cooled to room temperature and diluted with EtOAc (300 mL). The mixture was filtered through a pad of silica gel and the filtrate was concentrated in vacuo and the residue recrystallized from MeOH (15 g, 52%); MS (ES) m/z 229.0 (M+H)+.

Source