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

HRID 2404845Notes

Reaction equation

HRID 2404845 reaction equation
C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][C:28]=1[NH:37][CH:38]=[C:39]([C:45](OCC)=[O:46])[C:40]([O:42][CH2:43][CH3:44])=[O:41]>CCCCCC>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([F:34])([F:35])[F:36])=[C:29]2[C:28]=1[NH:37][CH:38]=[C:39]([C:40]([O:42][CH2:43][CH3:44])=[O:41])[C:45]2=[O:46]

Participants

4

Reactant 2

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

Product 1

HCID 13337379Ethyl 8-chloro-4-oxo-5-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylateYield 65.3%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

6 mL of Dowtherm was added to a long-neck 25 mL flask, fitted with a reflux condenser. The Dowtherm was heated to 200° C. and degassed for 20 minutes. Diethyl 2-((2-chloro-5-(trifluoromethyl)phenylamino)methylene)malonate (1 g, 2.73 mmol) was then added and the solution was then heated to reflux for 2.5 h under N2. The reaction mixture was cooled after 2.5 h, then diluted with hexane (12 mL) to produce a fine, light brown precipitate. The reaction mixture was filtered, and the precipitate washed with hexane until the color was removed. The product was air dried to obtain ethyl 8-chloro-4-oxo-5-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylate as a light brown solid (0.57 g, 65%). 1H NMR (400 MHz, DMSO-d6) δ 11.91 (s, 1H), 8.39 (s, 1H), 8.06 (d, J=8.3 Hz, 1H), 7.81 (d, J=8.4 Hz, 1H), 4.24 (q, J=7.1 Hz, 2H), 1.29 (t, J=7.1 Hz, 3H).

Workup

  1. customfitted with a reflux condenser
  2. customdegassed for 20 minutes
  3. temperaturethe solution was then heated
  4. temperatureto reflux for 2.5 h under N2
  5. temperatureThe reaction mixture was cooled after 2.5 h
  6. customto produce a fine, light brown precipitate
  7. filtrationThe reaction mixture was filtered
  8. washthe precipitate washed with hexane until the color
  9. customwas removed
  10. customdried

Sources & evidence

ORD record
ord-a757395fc7884df384ca63b527619017
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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