1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → Ethyl 8-chloro-4-oxo-5-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylate

HRID 1799498Notes

Reaction equation

HRID 1799498 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[NH:12][CH:13]=[C:14]([C:20](OCC)=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16].C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:10])[F:11])=[C:4]2[C:3]=1[NH:12][CH:13]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:20]2=[O:21]

Participants

3

Reactant 2

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 2797069Diethyl 2-((2-chloro-5-(trifluoromethyl)phenylamino)methylene)malonate

Product 1

HCID 13337379Ethyl 8-chloro-4-oxo-5-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylate

Conditions

Temperature
260 °C

Procedure

Compound 6B (2000 g, 5.468 mol) was introduced into the reactor. Dowtherm (4.000 L) was charged to the reactor and degassed at room temperature overnight with nitrogen purge. It was then stirred and warmed to 260° C. EtOH produced was distilled off. The reaction was monitored and was complete after 5.5 h, the reaction was substantially complete. Heat source was removed and the reaction mixture was cooled to 80° C. and heptane (2.000 L) was charged. The mixture was stirred for 30 min. Heptane (6.000 L) was charged to the stirred mixture and stirring continued overnight. Solids were filtered off and washed with heptane (4.000 L) and dried in a vacuum oven at 50° C. to provide Compound 6A.

Workup

  1. customdegassed at room temperature overnight with nitrogen
  2. custompurge
  3. customEtOH produced
  4. distillationwas distilled off
  5. temperatureHeat source
  6. customwas removed
  7. temperaturethe reaction mixture was cooled to 80° C.
  8. additionheptane (2.000 L) was charged
  9. stirringThe mixture was stirred for 30 min
  10. additionHeptane (6.000 L) was charged to the stirred mixture
  11. stirringstirring continued overnight
  12. filtrationSolids were filtered off
  13. washwashed with heptane (4.000 L)
  14. customdried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-0a2bf4b33449403ebc6fb227113858c0
Source dataset
uspto-grants-2013_01
Patent number
US08344147B2

Reaction notes

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