ChemicalBook CAS DataBase List 2-(2-HYDROXYETHYL)QUINOLINE

2-(2-HYDROXYETHYL)QUINOLINE synthesis

5synthesis methods

Product Name:2-(2-HYDROXYETHYL)QUINOLINE
CAS Number:1011-50-3
Molecular formula:C11H11NO
Molecular Weight:173.21

5100-57-2
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1011-50-3
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$58.00/100mg

Yield: 53%

Reaction Conditions:

Stage #1:ethyl 2-(2-quinolyl)acetate with lithium aluminium tetrahydride in diethyl ether at -78 - 20;
Stage #2: with Glauber's salt in methanol;diethyl ether at 0;

Steps:

4
2-fquinolin-2-yl)ethanol: Ethyl 2-quinolylacetate (8.6 g, 42.8 mmol) in diethyl ether (400 mL) was cooled to -78⁰C and lithium aluminum hydride (1.63 g, 42.8 mmol) was added portionwise. After stirring at -78°C for 2 h, the reaction mixture was allowed to warm slowly to O⁰C and was then stirred for 4 h at O⁰C followed by stirring at room temperature overnight. After cooling back to O⁰C, a small amount of methanol was added to quench remaining hydride followed by sodium sulfate decahydrate (43 g). After stirring at room temperature for 1 h, the mixture was filtered and the solid was washed with chloroform and was concentrated. Purification by silica gel chromatography (2:1 ethylacetate-hexanes) gave 0.46 g (53% yield) of the title compound; 13C NMR (101 MHz, CHLOROFORM-D) d ppm 161.53, 147.23, 137.04, 130.01 , 128.74, 127.79, 127.03, 126.39, 122.09, 61.60, 39.52; MS (AP/CI): 174.2 (M+H)+.

References:

PFIZER PRODUCTS INC. WO2008/20302, 2008, A2 Location in patent:Page/Page column 26