Diethyl (ethoxymethylene)malonate → Ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-xynoline carbonate

HRID 1360652Notes

Reaction equation

HRID 1360652 reaction equation
C(O[CH:4]=[C:5]([C:11]([O:13]CC)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[F:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][C:23]=1[F:24])[NH2:20].C1(OC2C=CC=CC=2)C=CC=CC=1>>[F:24][C:23]1[CH:22]=[C:21]2[C:19](=[CH:18][C:17]=1[F:16])[NH:20][CH:4]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:11]2=[O:13]

Participants

4

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 7583Diphenyl EtherHCID 774693,4-Difluoroaniline

Product 1

HCID 751784Ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-xynoline carbonate

Conditions

Temperature
130 °C

Procedure

Diethyl ethoxymethylenemalonate was added to 3,4-difluoroaniline at ambient temperature and the mixture was stirred at 130° C. for 17 hours. After diphenyl ether was additionally added to the reaction mixture, stirring was done at 260° C. for one hour. A solid obtained by leaving the reaction mixture to stand for cooling to ambient temperature was filtered, to obtain ethyl 6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate.

Workup

  1. stirringstirring
  2. waitwas done at 260° C. for one hour
  3. customA solid obtained
  4. customby leaving the reaction mixture
  5. temperaturefor cooling to ambient temperature
  6. filtrationwas filtered

Sources & evidence

ORD record
ord-9e9c407e4ed4439eb6cd7ce7282c8ab2
Source dataset
uspto-grants-2011_02
Patent number
US07879878B2

Reaction notes

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