6-ACETAMIDO-4-HYDROXY-2-METHYLQUINOLINE synthesis

4synthesis methods

Product Name:6-ACETAMIDO-4-HYDROXY-2-METHYLQUINOLINE
CAS Number:1140-81-4
Molecular formula:C12H12N2O2
Molecular Weight:216.24

(E)-Methyl 3-(4-acetaMidophenyliMino)butanoate

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1140-81-4
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Yield:1140-81-4 88%

Reaction Conditions:

in diphenylether at 245 - 260; for 0.25 h;

Steps:

N- (4-Hydroxy-2-methylquinolin-6-yl) acetamide (4): Phenyl ether (1 L) was heated to 255 °C. Butenoate 3 (334 g, 1.35 mol) was carefully added portionwise while maintaining temperature 245-260 °C. After the addition was complete, the yellow- orange suspension was held at 255 °C for an additional 15 min. The mixture was slowly cooled to 40 °C, the solids were collected by filtration and washed with EtOAc (3 x 500 mL) followed by MeOH (3 x 500 mL) to give hydroxy quinoline 4 as yellow-orange solid (256 g, 88% yield) ;'H NMR (DMSO) 5 11.52 (br, s, 1 H), 10.07 (s, 1 H), 8.24 (s, 1 H), 7.82 (d, 1 H), 7.42 (d, 1 H), 5.84 (s, 1 H), 2.31 (s, 3 H), 2.05 (s, 1 H)

References:

WO2005/51392,2005,A1 Location in patent:Page/Page column 46