Toluene → Ethyl 4-chloro-8-(trifluoromethyl)quinoline-3-carboxylate

HRID 2104474

Reaction equation

HRID 2104474 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1O)=[CH:13][CH:12]=[CH:11][C:10]=2[C:17]([F:20])([F:19])[F:18])=[O:5])[CH3:2].C1(C)C=CC=CC=1.O=P(Cl)(Cl)[Cl:30].C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:30])=[CH:13][CH:12]=[CH:11][C:10]=2[C:17]([F:20])([F:19])[F:18])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 1140TolueneHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178469613HCID 178469613, compound

Product 1

HCID 725465Ethyl 4-chloro-8-(trifluoromethyl)quinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Hydroxy-8-(trifluoromethyl)-3-quinolinecarboxylic acid ethyl ester (compound of formula (V)), 11.27 g, 39.55 mmol) was taken into toluene (125 mL), then POCl3 (7.4 mL, 79.08 mmol) was added and the mixture was refluxed for 1.5 hours. The reaction was carefully poured into ice-water with vigorous stirring, then added carefully added saturated NaHCO3 until the solution was neutral. Dilute with ethyl acetate and separate the layers. The organic layer was dried over MgSO4, filtered and concentrated. The resulting material was passed through a short silica gel plug using 10% ethyl acetate in hexane. Concentration and drying under high vacuum yielded 9.93 g of the title compound as a white solid.

Workup

  1. temperaturethe mixture was refluxed for 1.5 hours
  2. customseparate the layers
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. concentrationConcentration
  7. customdrying under high vacuum

Sources & evidence

ORD record
ord-c5a3fd7dce1d4682a2bb4285cef7041c
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Linked notes

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