ChemicalBook CAS DataBase List tasquinimod

tasquinimod synthesis

8synthesis methods

Product Name:tasquinimod
CAS Number:254964-60-8
Molecular formula:C20H17F3N2O4
Molecular Weight:406.36

Methyl 4-hydroxy-5-Methoxy-1-Methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate

1354639-61-4
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22864-65-9 Synthesis

22864-65-9
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254964-60-8
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Yield: 99%

Reaction Conditions:

in octane for 2 h;Product distribution / selectivity;Reflux;Molecular sieve;

Steps:

4
A mixture of 11 (5.00 g, 18.9 mmol), N-methyl-p-trifluoromethylaniline (5.13 g, 28.4 mmol) and n-octane (200 mL) were refluxed in a Soxhlet extraction apparatus containing 4A molecular sieves (22.9 g) for 2 hours. After cooling the mixture the product was isolated as above to furnish 7.6 g (99 %) of 4-hydroxy-5-methoxy-N,l-dimethyl-2-oxo-N-[(4- trifluoromethyl)phenyl] - 1 ,2-dihydroquino line-3 -carboxamide (C) . ¹ H-NMR analysis on the isolated product revealed no impurities other than 1 mol% remaining ester 11. 1 H-NMR (CDCI3) 9.9 (s, 1H), 7.50 (bs, 4H), 7.46 (t, 1H), 6.94 (d, 1H), 6.70 (d, 1H), 4.06 (s, 3H), 3.54 (s, 3H), 3.48 (s, 3H). When the same reaction was performed by the traditional distillation from n-octane (Entry 26) during 2 hours according to prior art US patent No. 6,875,869 the product was isolated in 94 % yield and determined by 1H-NMR analysis to consist of a mixture of compound C (96 mol%) and the starting material 11 (4 mol%).

References:

ACTIVE BIOTECH AB;BOCK, Lillemor Maria;HOLMBERG, Pär Henning;JANSSON, Karl-Erik WO2012/4338, 2012, A1 Location in patent:Page/Page column 13; 16

22864-65-9 Synthesis

22864-65-9
116 suppliers
$14.00/1g