Bromine → HCID 86601545, compound

HRID 1921023Notes

Reaction equation

HRID 1921023 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.[Br:12]Br>CC(O)=O>[Br:12][N:8]1[CH:3]2[C:2]([O:1][CH2:6][C:5](=[O:7])[NH:4]2)=[CH:11][CH:10]=[CH:9]1

Participants

4

Reactant 2

HCID 24408BromineHCID 884992H-pyrido(3,2-b)-1,4-oxazin-3(4H)-one

Product 1

HCID 86601545HCID 86601545, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one (5.00 g, 33.3 mmole) in HOAc (100 mL) was added Br2 (2.6 mL, 50.0 mmole). After stirring for 48 hours at RT, the reaction solution was concentrated to an orange solid, which was suspended in 1N NaOH (50 mL) and extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine and dried over Na2SO4. Flash chromatography on silica gel (9:1 CHCl3/MeOH containing 5% NH4OH) and drying under high vacuum gave the title compound (5.49 g, 72%) as a yellow solid: MS (ES) m/e 230 (M+H)+.

Workup

  1. concentrationthe reaction solution was concentrated to an orange solid, which
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. customFlash chromatography on silica gel (9:1 CHCl3/MeOH containing 5% NH4OH) and drying under high vacuum

Sources & evidence

ORD record
ord-4729b652068645f785945912aa1a0a57
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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