4-Fluoroaniline → 1-(4-Fluorophenyl)-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 703081Notes

Reaction equation

HRID 703081 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.F[C:10]1[C:22]([F:23])=[C:21]([F:24])[C:20]([F:25])=[CH:19][C:11]=1[C:12]([C:14](=[CH2:18])[C:15]([O-:17])=[O:16])=[O:13]>C(O)C>[F:25][C:20]1[CH:19]=[C:11]2[C:10](=[C:22]([F:23])[C:21]=1[F:24])[N:6]([C:5]1[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=1)[CH:18]=[C:14]([C:15]([OH:17])=[O:16])[C:12]2=[O:13]

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 867444562,3,4,5-Tetra-fluorobenzoyl-acrylate

Product 1

HCID 137283301-(4-Fluorophenyl)-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.7 g of 4-fluoroaniline are added dropwise to a solution of 16 g of ethyl 3-ethoxy-2-(2,3,4,5-tetra-fluorobenzoyl-acrylate (5) (X1 -X4 =F) (Appln. Ser. No. 756,469, filed July 18, 1985, now U.S. Pat. No. 4,952,695) in 50 ml of ethanol, while cooling with ice and stirring. The mixture is stirred at room temperature for 1 hour, 50 ml of ice-water are added and the precipitate is filtered off cold with suction, rinsed with water and dried at 50° C. over calcium chloride in vacuo. 16.5 g of (6) (R=4-fluorophenyl, X1 -X4 =F) of melting point 93°-95° C. are obtained.

Workup

  1. stirringThe mixture is stirred at room temperature for 1 hour
  2. filtrationthe precipitate is filtered off cold with suction
  3. washrinsed with water
  4. dry with materialdried at 50° C. over calcium chloride in vacuo

Sources & evidence

ORD record
ord-95679a45a3bf492d909a7f6c08dd9a44
Source dataset
uspto-grants-1991_01
Patent number
US04981854

Reaction notes

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