Sodium Hydroxide → 7-fluoro-1H-pyrido[2,3-b][1,4]oxazin-2-one

HRID 1943756Notes

Reaction equation

HRID 1943756 reaction equation
C[O:2][C:3](=O)[CH2:4][O:5][C:6]1[C:11]([N+:12]([O-])=O)=[CH:10][C:9]([F:15])=[CH:8][N:7]=1.[Sn](Cl)(Cl)(Cl)Cl.[OH-].[Na+]>Cl>[F:15][C:9]1[CH:8]=[N:7][C:6]2[O:5][CH2:4][C:3](=[O:2])[NH:12][C:11]=2[CH:10]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24287Tin tetrachlorideHCID 66936775(5-Fluoro-3-nitro-pyridin-2-yloxy)-acetic acid methyl ester

Product 1

HCID 669368177-fluoro-1H-pyrido[2,3-b][1,4]oxazin-2-oneYield 71%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

In a 250 ml round flask, (5-fluoro-3-nitro-pyridin-2-yloxy)-acetic acid methyl ester (1.35 g, 5.87 mmol) and tin tetrachloride (4.45 g, 23.48 mmol) were dissolved in 15 ml of concentrated hydrochloric acid, and then stirred at 80 t for 1 hour. The reaction mixture was cooled to room temperature, neutralized with 10% sodium hydroxide solution, and extracted with ethyl acetate. The combined organic layer was washed with water and saturated saline solution, dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The resulting solid was recrystallized from tetrahydrofuran and methanol to obtain 7-fluoro-1H-pyrido[2,3-b][1,4]oxazin-2-one as beige solid (0.70 g, 71%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with water and saturated saline solution
  3. dry with materialdried over anhydrous sodium sulfate (Na2SO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe resulting solid was recrystallized from tetrahydrofuran and methanol

Sources & evidence

ORD record
ord-bb2b1055de4e46bcb793b3d9a5226c35
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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