Trifluoroacetic acid → Ethyl 1-(6-amino-3,5-difluoropyridin-2-yl)-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1274767Notes

Reaction equation

HRID 1274767 reaction equation
[F:1][C:2]1[C:3]([N:19]2[C:28]3[C:23](=[C:24]([F:32])[C:25]([F:31])=[C:26]([F:30])[C:27]=3[F:29])[C:22](=[O:33])[C:21]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:20]2)=[N:4][C:5]([NH:9]CC2C=CC(OC)=CC=2)=[C:6]([F:8])[CH:7]=1.FC(F)(F)C(O)=O>>[NH2:9][C:5]1[N:4]=[C:3]([N:19]2[C:28]3[C:23](=[C:24]([F:32])[C:25]([F:31])=[C:26]([F:30])[C:27]=3[F:29])[C:22](=[O:33])[C:21]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:20]2)[C:2]([F:1])=[CH:7][C:6]=1[F:8]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22121224Ethyl 1-[3,5-difluoro-6-(p-methoxybenzylamino)pyridin-2-yl]-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 22121241Ethyl 1-(6-amino-3,5-difluoropyridin-2-yl)-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 114.5%

Procedure

To 1080 mg of ethyl 1-[3,5-difluoro-6-(p-methoxybenzylamino)pyridine-2-yl]-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate was added 4 ml of trifluoroacetic acid, and the mixture was allowed to stand at room temperature for 30 minutes. The solution was concentrated under reduced pressure, and 4 ml of ethanol was added to the residue, and the solution was again concentrated under reduced pressure. The precipitate was dispersed in ethanol, collected by filtration, and washed with ethanol to obtain 960 mg of the title compound as a gray powder.

Workup

  1. concentrationThe solution was concentrated under reduced pressure, and 4 ml of ethanol
  2. additionwas added to the residue
  3. concentrationthe solution was again concentrated under reduced pressure
  4. additionThe precipitate was dispersed in ethanol
  5. filtrationcollected by filtration
  6. washwashed with ethanol

Sources & evidence

ORD record
ord-05634b3817954397ac4bf55676532613
Source dataset
uspto-grants-2000_12
Patent number
US06156903

Reaction notes

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