Water → HCID 66936850, compound

HRID 1943713Notes

Reaction equation

HRID 1943713 reaction equation
[NH:1]1[C:14]2[CH:13]=[N:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[O:4][CH2:3][C:2]1=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[NH:1]1[C:14]2[CH:13]=[N:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66936864HCID 66936864, compound

Product 1

HCID 66936850HCID 66936850, compoundYield 10.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1H-4-oxa-1,9-diaza-phenanthren-2-one (526 mg, 2.63 mmol) was dissolved in tetrahydrofuran (13 ml) and then cooled to 0□. To the reaction mixture, 1.0M Lithium aluminum hydride dissolved in tetrahydrofuran (5.5 ml, 5.26 mmol) was added dropwise and stirred at room temperature for 2 hours. After completion of reaction, water (1 ml), 10% aqueous solution of sodium hydroxide (2 ml) and water (3 ml) were added thereto dropwise in this order and then stirred for 1 hour at room temperature. 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 (52 mg, 10.6%).

Workup

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

Sources & evidence

ORD record
ord-371cc200ad9b431296c290bb191fb7b1
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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