Ethyl (6-bromo-2-nitropyridin-3-yloxy)acetate → 6-Bromo-2H-pyrido[3,2-B][1,4]oxazin-3(4H)-one

HRID 734220Notes

Reaction equation

[Br:1][C:2]1[N:7]=[C:6]([N+:8]([O-])=O)[C:5]([O:11][CH2:12][C:13]([O:15]CC)=O)=[CH:4][CH:3]=1>CC(O)=O.CCOC(C)=O.[Fe]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:12][C:13](=[O:15])[NH:8][C:6]=2[N:7]=1

Participants

Conditions

Temperature: 90 °C

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 h, 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)+.

Workup

temperaturewas cooled to room temperature
filtrationThe mixture was filtered through a pad of silica gel
concentrationthe filtrate was concentrated in vacuo
customthe residue recrystallized from MeOH (15 g, 52%)

Sources & evidence

ORD record: ord-8d41c8066eea43c4b42faa2259e5399d
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592334B2

Reaction notes

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