Water → 7-trifluoromethyl-1H-pyrido[2,3-b][1,4]oxazin-2-one

HRID 1943657Notes

Reaction equation

HRID 1943657 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]([C:15]([F:18])([F:17])[F:16])=[CH:8][N:7]=1.[Sn](Cl)(Cl)(Cl)Cl.O>Cl>[F:16][C:15]([F:18])([F:17])[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 962WaterHCID 24287Tin tetrachlorideHCID 66936440(3-Nitro-5-trifluoromethyl-pyridin-2-yloxy)-acetic acid methyl ester

Product 1

HCID 669364877-trifluoromethyl-1H-pyrido[2,3-b][1,4]oxazin-2-oneYield 62%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

In a 10 ml flask, (3-nitro-5-trifluoromethyl-pyridin-2-yloxy)-acetic acid methyl ester (84 mg, 0.30 mmol) was dissolved in concentrated hydrochloric acid (1.5 ml) and then tin tetrachloride (227 mg, 1.2 mmol) was added thereto. The mixture was stirred for 30 minutes at 80□. After completion of the reaction, water was added thereto at room temperature and the mixture was extracted with a solvent of methanol: dichloromethane=1:9. 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 (40 mg, 62%).

Workup

  1. additionwas added
  2. extractionat room temperature and the mixture was extracted with a solvent of methanol
  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-c69f8e450071457faa9239e8ddd480b6
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

Loading…