Water → 2H,3H,4H-pyrido[4,3-b][1,4]oxazine

HRID 1943629Notes

Reaction equation

HRID 1943629 reaction equation
[O:1]1[CH2:6][C:5](=O)[NH:4][C:3]2[CH:8]=[N:9][CH:10]=[CH:11][C:2]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[O:1]1[CH2:6][CH2:5][NH:4][C:3]2[CH:8]=[N:9][CH:10]=[CH:11][C:2]1=2

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 144799002H,3H,4H-pyrido[4,3-b][1,4]oxazin-3-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 218859502H,3H,4H-pyrido[4,3-b][1,4]oxazineYield 91.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4H-pyrido[4,3-b][1,4]oxazin-3-one (4.3 g, 28 mmol) was dissolved in tetrahydrofuran (140 ml) and then cooled to 0□. 1.0M Lithium aluminum hydride dissolved in tetrahydrofuran (57 ml, 57 mmol) was added thereto dropwise. After stirring for 2 hours at room temperature, 1.4 ml of water, 2.8 ml of 10% aqueous solution of sodium hydroxide, and 4.2 ml of water were added in this order under stirring. After filtering precipitates, the filtrate was extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on amine silica eluting with a solvent of dichloromethane. The fractions containing the product were collected and evaporated to obtain colorless liquid (3.5 g, 91%).

Workup

  1. temperaturecooled to 0□
  2. additionwas added
  3. stirringunder stirring
  4. filtrationAfter filtering
  5. customprecipitates
  6. extractionthe filtrate was extracted with ethyl acetate
  7. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe residue was purified by column chromatography on amine silica eluting with a solvent of dichloromethane
  11. additionThe fractions containing the product
  12. customwere collected
  13. customevaporated

Sources & evidence

ORD record
ord-a420717be20147f5a8c4cc5b5d087a65
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

Loading…