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

HRID 1111339Notes

Reaction equation

HRID 1111339 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C(O[CH:12]=[C:13]([C:19](=[O:30])[C:20]1[CH:25]=[C:24]([F:26])[C:23]([F:27])=[C:22]([F:28])[C:21]=1F)[C:14]([O:16]CC)=[O:15])C>C(O)C>[F:26][C:24]1[CH:25]=[C:20]2[C:21](=[C:22]([F:28])[C:23]=1[F:27])[N:6]([C:5]1[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=1)[CH:12]=[C:13]([C:14]([OH:16])=[O:15])[C:19]2=[O:30]

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 54346083Ethyl 3-ethoxy-2-(2,3,4,5-tetrafluorobenzoyl)acrylate

Product 1

HCID 137283301-(4-Fluorophenyl)-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 97.9%

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 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-aced9f851e8e4ac2affde60d6d067d7f
Source dataset
uspto-grants-1990_12
Patent number
US04980353

Reaction notes

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