Water → 7-bromo-2H,3H,4H-pyrido(3,2-b)(1,4)oxazin-3-one

HRID 1255952Notes

Reaction equation

HRID 1255952 reaction equation
[O:1]1[CH2:6][C:5](=[O:7])[NH:4][C:3]2[N:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.C1C(=O)N([Br:19])C(=O)C1.O>CN(C=O)C>[Br:19][C:10]1[CH:9]=[N:8][C:3]2[NH:4][C:5](=[O:7])[CH2:6][O:1][C:2]=2[CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimide2×HCID 884992H-pyrido(3,2-b)-1,4-oxazin-3(4H)-one

Product 1

HCID 159259837-bromo-2H,3H,4H-pyrido(3,2-b)(1,4)oxazin-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2H-pyrido[3,2-b][1,4]oxazin-3-one (0.75 g, 5 mmol) in DMF (18 mL) was slowly added NBS (1.07 g, 6 mmol) under N2. The mixture was stirred at rt for 16 h. HPLC indicated 75% conversion. More NBS (0.53 g, 3 mmol) was added and the mixture was stirred for another 24 h. Water (5 mL) was added and the reaction flask was chilled. The white solid which separated was filtered and washed with EtOAc, H2O, Et2O, and dried under vacuum in the presence of PBS and then used directly in the next step (687 mg, 60%).

Workup

  1. stirringthe mixture was stirred for another 24 h
  2. temperaturethe reaction flask was chilled
  3. customThe white solid which separated
  4. filtrationwas filtered
  5. washwashed with EtOAc, H2O, Et2O
  6. customdried under vacuum in the presence of PBS

Sources & evidence

ORD record
ord-373caff7346e430b8c443a07015ce463
Source dataset
uspto-grants-2013_06
Patent number
US08461167B2

Reaction notes

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