ChemicalBook CAS DataBase List 4-HYDROXY-2-METHYLQUINOLINE

4-HYDROXY-2-METHYLQUINOLINE synthesis

11synthesis methods

Product Name:4-HYDROXY-2-METHYLQUINOLINE
CAS Number:5660-24-2
Molecular formula:C10H9NO
Molecular Weight:159.18

Butanoic acid, 3-(phenylimino)-, ethyl ester, (3Z)-

1100207-42-8
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5660-24-2
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Yield:5660-24-2 53%

Reaction Conditions:

in diphenylether at 255; for 0.5 h;

Steps:

7
2-methylquinolin-4(1H)-one. (Z)-ethyl 3-(phenylimino)butanoate (6.26 g, 30.49 mmol) was cyclized in diphenyl ether (30 ml) by heating at 255° C. for 30 minutes. After cooling to room temperature a precipitate formed. The precipitate was filtered and washed several times with ether to remove any traces of phenyl ether to afford intermediate 7 (2.6 g, 16.3 mmol, 53%). ¹H NMR (400 MHz, MeOD) δ ppm 8.12 (d, J=8.06 Hz, 1H), 7.55-7.66 (m, 1H), 7.46 (d, J=8.31 Hz, 1H), 7.31 (t, J=7.68 Hz, 1H), 6.13 (s, 1H), 2.39 (s, 3H). Mass 159 [M+H]⁺.

References:

Bristol-Myers Squibb Company US2009/18163, 2009, A1 Location in patent:Page/Page column 24-25

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141-97-9 Synthesis