2,4-Difluoroaniline → HCID 18549168, compound

HRID 1266173Notes

Reaction equation

HRID 1266173 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].Cl[C:11]1[C:20]([C:21](=[O:32])[C:22](=[CH:28]N(C)C)[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:19][C:18]2[C:13](=[C:14]([F:35])[C:15]([F:34])=[C:16]([F:33])[CH:17]=2)[N:12]=1>ClC(Cl)Cl>[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[N:4]1[C:11]2[N:12]=[C:13]3[C:14]([F:35])=[C:15]([F:34])[C:16]([F:33])=[CH:17][C:18]3=[CH:19][C:20]=2[C:21](=[O:32])[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:28]1

Participants

4

Reactant 2

HCID 97092,4-DifluoroanilineHCID 53994177Ethyl 2-(2-chloro-6,7,8-trifluoro-3-quinolinecarbonyl)(dimethylamino)acrylate

Product 1

HCID 18549168HCID 18549168, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

5.2 g of 2,4-difluoroaniline were added, at a temperature around 20° C., to a solution of 7.7 g of ethyl 3-(2-chloro-6,7,8-trifluoro-3-quinolyl)-2-dimethylaminomethylene-3-oxopropionate in 50 cm3 of trichloromethane and the reaction mixture was left stirring at this temperature for 8 hours. The trichloromethane was concentrated under reduced pressure (20 kPa) at a temperature around 40° C. 120 cm3 of ethanol and 4.5 cm3 of 1,8-diazabicyclo[5.4.0]undec-7-ene were added to the mixture, which was heated at a temperature around 80° C. for approximately 1 hour. After cooling to a temperature around 10° C., the product was filtered off and washed 2 times with 50 cm3 of ethanol and 2 times with 50 cm3 of isopropyl ether. 5 g of ethyl 1-(2,4-difluorophenyl)-7,8,9-trifluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate were obtained in the form of a yellow solid melting at about 304-306° C., which solid was used without additional purification in the subsequent stages.

Workup

  1. waitthe reaction mixture was left
  2. concentrationThe trichloromethane was concentrated under reduced pressure (20 kPa) at a temperature around 40° C
  3. addition120 cm3 of ethanol and 4.5 cm3 of 1,8-diazabicyclo[5.4.0]undec-7-ene were added to the mixture, which
  4. temperatureAfter cooling to a temperature around 10° C.
  5. filtrationthe product was filtered off
  6. washwashed 2 times with 50 cm3 of ethanol and 2 times with 50 cm3 of isopropyl ether

Sources & evidence

ORD record
ord-9392a8548a1e4d48be507c92804dce74
Source dataset
uspto-grants-2003_04
Patent number
US06548506B2

Reaction notes

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