Water → 7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine

HRID 1943651Notes

Reaction equation

HRID 1943651 reaction equation
[C:1]1([C:7]2[CH:17]=[N:16][C:10]3[O:11][CH2:12][C:13](=O)[NH:14][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[C:1]1([C:7]2[CH:17]=[N:16][C:10]3[O:11][CH2:12][CH2:13][NH:14][C:9]=3[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 669367437-Phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

Product 1

HCID 669365097-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazineYield 52.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2-one (21 mg, 0.09 mmol) was dissolved in tetrahydrofuran (0.5 ml) and then cooled to 0□. 1.0M Lithium aluminum hydride dissolved in tetrahydrofuran (0.19 ml, 0.19 mmol) was added thereto dropwise. After stirring for 5 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. The residue was purified by column chromatography on silica eluting with a solvent of dichloromethane:methanol=40:1. The fractions containing the product were collected and evaporated to obtain pale-grey solid (10 mg, 50%).

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 silica eluting with a solvent of dichloromethane
  11. additionThe fractions containing the product
  12. customwere collected
  13. customevaporated

Sources & evidence

ORD record
ord-1ed3c4801a5c4515964eaf145e19f487
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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