Water → 7-Trifluoromethyl-2,3-dihydro-1H-pyrido[2,3-B][1,4]oxazine

HRID 1943658Notes

Reaction equation

HRID 1943658 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[N:12][C:6]2[O:7][CH2:8][C:9](=O)[NH:10][C:5]=2[CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(=O)([O-])O.[Na+]>O1CCCC1>[F:14][C:2]([F:1])([F:15])[C:3]1[CH:13]=[N:12][C:6]2[O:7][CH2:8][CH2:9][NH:10][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 669364877-trifluoromethyl-1H-pyrido[2,3-b][1,4]oxazin-2-one

Product 1

HCID 669366917-Trifluoromethyl-2,3-dihydro-1H-pyrido[2,3-B][1,4]oxazineYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a 5 ml flask, 7-trifluoromethyl-1H-pyrido[2,3-b][1,4]oxazin-2-one (60 mg, 0.28 mmol) was dissolved in tetrahydrofuran (1.0 ml), and then 1.0M Lithium aluminum hydride dissolved in tetrahydrofuran (0.33 ml, 0.33 mmol) was added thereto dropwise and stirred for 1 hour at 0□. Water and saturated solution of sodium hydrogen carbonate were added and the mixture 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 methanol:dichloromethane=1:50. The fractions containing the product were collected and evaporated to obtain white solid (29 mg, 52%).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica eluting with a solvent of methanol
  7. additionThe fractions containing the product
  8. customwere collected
  9. customevaporated

Sources & evidence

ORD record
ord-25adcc25b0394b389ceb85a71a051ec0
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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