5,7-DICHLORO-4-HYDROXY-QUINOLINE-2-CARBOXYLIC ACID ETHYL ESTER synthesis

4synthesis methods

Product Name:5,7-DICHLORO-4-HYDROXY-QUINOLINE-2-CARBOXYLIC ACID ETHYL ESTER
CAS Number:166981-79-9
Molecular formula:C12H9Cl2NO3
Molecular Weight:286.11

2-Butenedioic acid, 2-[(3,5-dichlorophenyl)amino]-, 1,4-diethyl ester, (2Z)-

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5,7-DICHLORO-4-HYDROXY-QUINOLINE-2-CARBOXYLIC ACID ETHYL ESTER

166981-79-9
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Yield:166981-79-9 85.8%

Reaction Conditions:

with diphenylether at 244; for 0.166667 h;

Steps:

2

A 5-L three-neck flask equipped with a thermocouple, an addition runnel, and a distillation apparatus was charged with diphenyl ether (about 2.8 L), which was heated to about 244 °C. The concentrated reaction mixture containing Compound 3 (about 1.1 mole) from Reaction 1, above, was added from the dropping funnel into the hot diphenyl ether over about 10 minutes with a nitrogen purge. The funnel was rinsed with about 200 mL of diphenyl ether, which was also added to the flask. The resulting mixture was heated at about 244 ⁰C for about 1 hour to cyclize Compound 3 to form Compound 4. The reaction mixture then was cooled to room temperature, at which point Compound 4 crystallized out. The crystallized product was isolated and slurried with ethyl acetate (EtOAc; about 1 L). The crystals were collected and rinsed with EtOAc (3 x 500 mL), and then dried under high vacuum at room temperature to afford about 269.95 g of Compound 4 (85.8 % yield over two steps).

References:

WO2007/44682,2007,A2 Location in patent:Page/Page column 9

2-Quinolinecarboxylic acid, 5,7-dichloro-4-(phenylmethoxy)-, ethyl ester

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