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ChemicalBook CAS DataBase List ETHYL 4-HYDROXY-6-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLATE
26893-12-9

ETHYL 4-HYDROXY-6-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLATE synthesis

4synthesis methods
(4-TRIFLUOROMETHYLPHENYLAMINO)METHYLENEMALONIC ACID DIETHYL ESTER

49713-39-5

ETHYL 4-HYDROXY-6-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLATE

26893-12-9

GENERAL METHODS: Polyphosphoric acid (PPA) (2 eq. by weight) was mixed with Intermediate 1 (40 mmol), followed by the addition of phosphoryl chloride (POCl3) (10 mmol). The reaction mixture was heated to 75 °C and maintained for 8 h. The reaction progress was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was quenched by slowly pouring it into 10% sodium hydroxide solution in an ice bath while adjusting the pH to about 7. The resulting solid was separated by filtration, dried, and washed with ether (3 x 20 mL) to afford ethyl 4-hydroxy-6-trifluoromethylquinoline-3-carboxylate in good yield.

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Yield:26893-12-9 73%

Reaction Conditions:

in diphenylether;Reflux;Gould-Jacobs reaction;

References:

Niedermeier, Sabine;Singethan, Katrin;Rohrer, Sebastian G.;Matz, Magnus;Kossner, Markus;Diederich, Sandra;Maisner, Andrea;Schmitz, Jens;Hiltensperger, Georg;Baumann, Knut;Holzgrabe, Ulrike;Schneider-Schaulies, Jurgen [Journal of Medicinal Chemistry,2009,vol. 52,# 14,p. 4257 - 4265] Location in patent:supporting information; experimental part

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