1-Ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → HCID 14839365, compound

HRID 2165620Notes

Reaction equation

HRID 2165620 reaction equation
[F:1][CH2:2][CH:3]1[CH2:8][NH:7][CH2:6][CH2:5][NH:4]1.[CH2:9]([N:11]1[C:20]2[C:15](=[CH:16][C:17]([F:22])=[C:18](F)[CH:19]=2)[C:14](=[O:23])[C:13]([C:24]([OH:26])=[O:25])=[CH:12]1)[CH3:10]>N1C=CC=CC=1>[CH2:9]([N:11]1[C:20]2[C:15](=[CH:16][C:17]([F:22])=[C:18]([N:7]3[CH2:6][CH2:5][NH:4][CH:3]([CH2:2][F:1])[CH2:8]3)[CH:19]=2)[C:14](=[O:23])[C:13]([C:24]([OH:26])=[O:25])=[CH:12]1)[CH3:10]

Participants

4

Reactant 2

HCID 8005211-Ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 14479501HCID 14479501, compound

Product 1

HCID 14839365HCID 14839365, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 400 mg of 2-(fluoromethyl)piperazine and 200 mg of 1-ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in 3 ml of pyridine was stirred and heated at 75° C., under nitrogen, in a pressure bottle for 3 hours. The pyridine was removed and replaced with methanol. This mixture was chromatographed on silica gel, eluting with methanol:chloroform (2:8). The solid was recrystallized from methanol, giving 100 mg of the desired product, mp 177°-180° C.

Workup

  1. customThe pyridine was removed
  2. customThis mixture was chromatographed on silica gel
  3. washeluting with methanol:chloroform (2:8)
  4. customThe solid was recrystallized from methanol

Sources & evidence

ORD record
ord-3948b0bc3c2843e78761ce440ffb61ed
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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