Potassium Fluoride → Ethyl 6,7,8-trifluoro-1-(methylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1708542Notes

Reaction equation

HRID 1708542 reaction equation
F[C:2]1[C:26]([F:27])=[C:25]([F:28])[C:24]([F:29])=[CH:23][C:3]=1[C:4]([C:6](=[CH:12][NH:13][N:14](C(OC(C)(C)C)=O)[CH3:15])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[F-].[K+]>CN(C)C=O>[F:27][C:26]1[CH:2]=[C:3]2[C:23](=[C:24]([F:29])[C:25]=1[F:28])[N:13]([NH:14][CH3:15])[CH:12]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:4]2=[O:5]

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 178472138HCID 178472138, compound

Product 1

HCID 11098599Ethyl 6,7,8-trifluoro-1-(methylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 87.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 2-(2,3,4,5-tetrafluorobenzoyl)-3-(2-tert-butoxycarbonyl-2-methylhydrazino)acrylate (2.00 g) and potassium fluoride (0.31 g) in dimethylformamide(5 ml) was heated at 60°~65° C. for one hour, and refluxed for 5 hours. The mixture was poured into ice-water (60 ml) to give a solid. The solid was collected by filtration and dried over phosphorus pentaoxide under reduced pressure to give ethyl 6,7,8-trifluoro-1-methylamino-1,4-dihydro-4-oxoquinoline-3-carboxylate (1.25 g).

Workup

  1. temperaturewas heated at 60°~65° C. for one hour
  2. temperaturerefluxed for 5 hours
  3. customto give a solid
  4. filtrationThe solid was collected by filtration
  5. dry with materialdried over phosphorus pentaoxide under reduced pressure

Sources & evidence

ORD record
ord-9dd2e90475824e24ad5891c322a44976
Source dataset
uspto-grants-1994_10
Patent number
US05359066

Reaction notes

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