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ChemicalBook CAS DataBase List 2,4-Dichloro-7-methoxy-8-methylquinoline
1108659-32-0

2,4-Dichloro-7-methoxy-8-methylquinoline synthesis

2synthesis methods
-

Yield:1108659-32-0 43%

Reaction Conditions:

with trichlorophosphate for 16 h;Heating / reflux;

Steps:

14.1; 13.B.3

Step 1: Preparation of 2,4-dichloro-8-methyl-7-methoxyquinoline 81. A mixture of 2-methyl-3-methoxyaniline hydrochloride (15 g, 1 eq.), malonic acid (12.06 g, 1.5 eq.), and phosphorus oxochloride (80 mL) was refluxed for 16 hrs. The reaction mixture was slowly poured into water and extracted with DCM. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified on silica pad (eluted with DCM) to yield compound 81 as a white powder in 43% yield. 1H NMR (CDCl3, 376 MHz) δ 2.62 (s, 3H), 4.03 (s, 3H), 7.34 (s, IH), 7.37 (d, J = 9.02 Hz, IH), 8.05 (d, J = 9.02 Hz, IH).

References:

WO2009/14730,2009,A1 Location in patent:Page/Page column 123; 126-127