3-Quinolinecarboxylic acid, 4-hydroxy-8-(trifluoromethyl)-, ethyl ester

General procedure: Diethyl ({[(trifluoromethyl)phenyl]amino}methylidene)propanedioate 2a, b (10.0 g, 0.030 mol) and Dowtherm (100 mL) were heated to 250 °C for 5 h. The reaction mixture was then cooled to 25 °C and stirred in 150 mL hexane for 10 min. The solid product obtained was filtered and dried. The crude product obtained was purified by column chromatography using pet ether and ethyl acetate (5:5) as the eluent to get white solids.Diethyl 2-[(2-trifluoromethyl-phenylamino)-methylene]-malonic acid diethyl ester (2) (10.0g, 0.030mol) and Dowtherm (100mL) were heated to 250°C for 5h. The reaction mixture was then cooled to 25°C and stirred in 150mL of hexane for 10min. The solid product obtained was filtered and dried. The crude product was purified by column chromatography using pet ether and ethyl acetate (5:5) as the eluent to get white solids. Yield: (8.1g, 94.1percent). M.p: 295–297°C. IR (neat νDiethyl 2-({[2-(trifluoromethyl)phenyl]amino}methylene)malonate (compound of formula (IV)), 69.73 g, 210.5 mmol) was taken into Dowtherm A (350 mL) and brought to reflux (-250° C.) with the removal of ethanol that was formed during the reaction for 45 min. The reaction was allowed to cool to approximately 100° C. then carefully poured into hexane (1 L) and allowed to cool overnight. A white solid precipitated which was filtered and dried to afford the title compound as a white solid (55.04 g, 91.7percent). MS ESI (m/z) 286 ([M+H]Compound 2 (9 g, 27 mmol) was heated at 250 °C for 4 h in Dowtherm medium. The reaction mixture was cooled to 26 °C and added hexane (200 mL) and stirred for 15 min, the precipitated solid was filtered and dried to get compound 3 as a white solid 3.5 g (45percent yield). IR (KBr, cm (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.To a suspension of A mixture of

Molecular Weight:285.22
XLogP3:2.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:3
Exact Mass:285.06127767
Monoisotopic Mass:285.06127767
Topological Polar Surface Area:55.4
Heavy Atom Count:20
Complexity:445
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes