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

HRID 1943626Notes

Reaction equation

HRID 1943626 reaction equation
[NH:1]1[C:6](=O)[CH2:5][O:4][C:3]2[N:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[NH:1]1[CH2:6][CH2:5][O:4][C:3]2[N:8]=[CH:9][CH:10]=[CH:11][C:2]1=2

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 159259881H,2H,3H-pyrido(2,3-b)(1,4)oxazin-2-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 151279022,3-Dihydro-1H-pyrido[2,3-b][1,4]oxazineYield 88.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1H-pyrido[2,3-b][1,4]oxazin-2-one (113 mg, 0.75 mmol) was dissolved in tetrahydrofuran (3.5 ml) and then cooled to 0□. 1.0M Lithium aluminum hydride dissolved in tetrahydrofuran (1.5 ml, 1.5 mmol) was added thereto dropwise. After stirring for 2 hours at room temperature, 0.1 ml of water, 0.2 ml of 10% aqueous solution of sodium hydroxide, and 0.3 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 to obtain colorless liquid (90 mg, 88%).

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

Sources & evidence

ORD record
ord-9b39bdf8a3164714a71fc4810a2a0710
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

Loading…