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

HRID 1952186Notes

Reaction equation

HRID 1952186 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 14 (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 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 15.

Workup

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

Sources & evidence

ORD record
ord-4c504e58688c4baa81d7c9a400016df7
Source dataset
uspto-grants-2013_03
Patent number
US08404849B2

Reaction notes

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