ethyl 4-hydroxy-5-(trifluoromethyl)quinoline-3-carboxylate synthesis

5synthesis methods

Product Name:ethyl 4-hydroxy-5-(trifluoromethyl)quinoline-3-carboxylate
CAS Number:56881-18-6
Molecular formula:C13H10F3NO3
Molecular Weight:285.22

Ethyl 8-chloro-4-hydroxy-5-(trifluoromethyl)-3-quinolinecarboxylate

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ethyl 4-hydroxy-5-(trifluoromethyl)quinoline-3-carboxylate

56881-18-6
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Yield:-

Reaction Conditions:

with hydrogen;triethylamine;palladium 10% on activated carbon in ethanol at 5; for 20 h;

Steps:

1

A3-neck, 5 -L flask was charged with of ethyl 8-chloro- 4-oxo-5-(trifluoromethyl)-l,4- dihydroquinoline-3-carboxylate 5 (100 g, 0.3 mol), ethanol (1250 mL, 12.5 ml/g) and triethylamine (220 mL, 1.6 mol). The vessel was then charged with 10 g of 10% Pd/C (50% wet) at 5 ⁰C. The reaction was stirred vigorously under hydrogen atmosphere for 20 h at 5 ⁰C, after which lime the reaction mixture was concentrated to a volume of approximately 150 mL. The product, ethyl 4-oxo-5-(rrifluoromeyl)-lH-quinoline-3-carboxylate 6, as a slurry with Pd/C, was taken directly into the next step.

References:

WO2010/48573,2010,A1 Location in patent:Page/Page column 30

121-50-6 Synthesis