Potassium Fluoride → Ethyl 9,10-difluoro-3-methyl-7-oxo-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate

HRID 1762319Notes

Reaction equation

HRID 1762319 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[C:5]([C:12](=[O:26])[C:13]1[CH:18]=[C:17]([F:19])[C:16]([F:20])=[C:15]([O:21][C:22](=O)C)[C:14]=1F)=[CH:6][NH:7][CH:8]([CH3:11])CO)[CH3:2].[F-].[K+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:5]1[C:12](=[O:26])[C:13]2[CH:18]=[C:17]([F:19])[C:16]([F:20])=[C:15]3[O:21][CH2:22][CH:8]([CH3:11])[N:7]([CH:6]=1)[C:14]=23)=[O:27])[CH3:2]

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 178472010ethyl 2-(3-acetyloxy-2,4,5-trifluorobenzoyl)-3-(1-hydroxypropan-2-ylamino)prop-2-enoate

Product 1

HCID 3751628Ethyl 9,10-difluoro-3-methyl-7-oxo-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylateYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 30 ml of dimethylformamide was dissolved 4.30 g of the ethyl-2-(3-acetoxy-2,4,5-trifluorobenzoyl)-3-(2-hydroxy-1-methylethyl)aminoacrylate (X) thus obtained and 1.92 g (0.033 mole) of potassium fluoride was added to the mixture and the mixture was stirred at 140° to 150° C. for 2 hours. After completion of the reaction, the solvent was distilled under reduced pressure. To the residue was added water and the mixture was extracted with dichloromethane, and the organic layer was washed with water, dried and then condensed under reduced pressure. Then, the residue was washed with ethanol, and the residue was recrystallized from acetone to give 1.40 g of ethyl-9,10-difluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylate (IV) as pale brown fine needle crystals.

Workup

  1. customthus obtained
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled under reduced pressure
  4. additionTo the residue was added water
  5. extractionthe mixture was extracted with dichloromethane
  6. washthe organic layer was washed with water
  7. customdried
  8. customcondensed under reduced pressure
  9. washThen, the residue was washed with ethanol
  10. customthe residue was recrystallized from acetone

Sources & evidence

ORD record
ord-7edc55c3e6a24893bf4114c66667b38d
Source dataset
uspto-grants-1989_05
Patent number
US04831190

Reaction notes

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