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

HRID 1943704Notes

Reaction equation

HRID 1943704 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([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:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([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]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 669367477-pyridin-3-yl-1H-pyrido[2,3-b][1,4]oxazin-2-one

Product 1

HCID 669368927-pyridin-3-yl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazineYield 53.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

7-pyridin-3-yl-1H-pyrido[2,3-b][1,4]oxazin-2-one (60 mg, 0.264 mmol) was dissolved in 4 ml of anhydrous tetrahydrofuran under nitrogen atmosphere, and the mixture was cooled to 0□, and 1.0M Lithium aluminum hydride dissolved in tetrahydrofuran (0.7 ml, 0.704 mmol) was added thereto dropwise at room temperature for 5 hours. To the reaction mixture, water (0.3 ml), 10% sodium hydroxide (0.6 ml) and water (0.9 ml) were added dropwise in this order, and then stirred vigorously at room temperature for 1 hour. The formed solid was filtered and washed with excess ethyl acetate. The filtrate was washed with water and saturated saline solution, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure to obtain 7-pyridin-3-yl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine as white solid (30 mg, 53%).

Workup

  1. additionwas added
  2. filtrationThe formed solid was filtered
  3. washwashed with excess ethyl acetate
  4. washThe filtrate was washed with water and saturated saline solution
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-03b2d08e267e4f238b59d3b8037c19ec
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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