4-Quinolinol, 6-(phenylMethoxy)- synthesis

Yield:-

Reaction Conditions:

at 100 - 250; for 2 h;DOWTHERM A heat transfer fluid;

Steps:

57.B; 150.B
A solution of 5- { [ (4-BENZYLOXY) phenylimino) ] METHYL}-2, 2-DIMETHYL- [1, 3] dioxane- 4,6-dione (127.2 g, 0.360 mol) and DOWTHERM A heat transfer fluid (500 mL) was heated to 100 °C and then slowly added to a flask containing DOWTHERM A heat transfer fluid (1 L, heated at 250 °C) over a period of 90 minutes. During the addition, the reaction temperature was not allowed to fall below 245 °C. Following the addition, the reaction was stirred at 250 °C FOR 30 minutes, and then allowed to cool to ambient temperature. A precipitate formed, which was isolated by filtration, washed with diethyl ether (1 L) and acetone (250 mL), and dried for two hours under vacuum in to provide 65.7 g of 6-benzyloxyquinolin-4-ol as a yellow powder. 'H NMR (300MHZ, DMSO-d6) : 8 11.72 (s, 1H), 7.84 (d, J= 7.3 Hz, 1H), 7.59 (m, 8H), 5.98 (d, J= 7.0 Hz, 1H), 5.18 (s, 2H).; Part B A solution of 5-F [ (4-BENZYLOXY) PHENYLIMINO)] MCTHYL}-2, 2-DIMETHYL- [1, 3] -dioxane- 4,6-dione (127.2 g) and DOWTHERM A (500 mL) heat transfer fluid was heated to 100 °C and then slowly added to a flask containing DOWTHERM A heat transfer fluid (1 L, heated at 250 °C) over a period of 90 minutes. During the addition, the reaction temperature was not allowed to fall below 245 °C. Following the addition, the reaction was stirred at 250 °C for 30 minutes, and then allowed to cool to ambient temperature. A precipitate formed, which was isolated by filtration, washed with diethyl ether (1 L) and acetone (250 mL), and dried for two hours under vacuum to provide 65.7 g OF 6- benzyloxyquinolin-4-ol as a yellow powder.

References:

3M INNOVATIVE PROPERTIES COMPANY WO2005/20999, 2005, A1 Location in patent:Page/Page column 39; 119; 224