Selenium Dioxide → HCID 86605556, compound

HRID 2374169Notes

Reaction equation

HRID 2374169 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH3:12])=[CH:9][CH:8]=[CH:7][N:6]=2.[O:13]1CCOCC1.[Se](=O)=O>O>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH:12]=[O:13])=[CH:9][CH:8]=[CH:7][N:6]=2

Participants

5

Reactant 3

HCID 24007Selenium DioxideHCID 312751,4-DioxaneHCID 68528911HCID 68528911, compound

Product 1

HCID 86605556HCID 86605556, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-bromo-4-methyl-[1,8]-naphthyridine (1.5 g, 6.7 mmol), dioxane (16 mL) and water (0.6 mL) was treated with selenium dioxide (3.0 g, 27 mmol) and stirred at 80° C. for 1 h. The mixture was cooled to RT, diluted with satd. aq. NaHCO3, extracted 3× with EtOAc, and the combined organic phases were dried over Na2SO4, filtered and concentrated under vacuum. Filtration through a pad of silica gel eluting with EtOAc gave 0.70 g of the title compound as a yellow solid. 1H NMR (CDCl3) δ 10.62 (s, 1H), 9.32 (s, 1H), 9.28 (d, 1H), 1.18 (d, 1H), 7.66 (dd, 1H).

Workup

  1. temperatureThe mixture was cooled to RT
  2. additiondiluted with satd
  3. extractionaq. NaHCO3, extracted 3× with EtOAc
  4. dry with materialthe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. filtrationFiltration through a pad of silica gel eluting with EtOAc

Sources & evidence

ORD record
ord-2081cc8820b34a3e83119c1138c56355
Source dataset
uspto-grants-2008_12
Patent number
US07462600B2

Reaction notes

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