反応 #9456

反応方程式

5-(Biphenyl-3-ylaminomethylene)-2,2-dimethyl-[1,3]dioxane-4,6-dione

→

7-phenylquinolin-4-ol

収率 96.7%

溶媒

DOWTHERM A

DOWTHERM A

反応条件

後処理

1. 1
   温度heat transfer fluid to 215° C
2. 2
   workup.ADDITIONAfter complete addition
3. 3
   温度cooled to RT
4. 4
   ろ過The resulting solid was collected by filtration
5. 5
   洗浄sequentially washed with diethyl ether (1.7 L) and acetone (500 mL)
6. 6
   その他dried in a vacuum oven at 70° C. overnight
7. 7
   ろ過Filtration of the slurry

実験手順

5-(Biphenyl-3-ylaminomethylene)-2,2-dimethyl-[1,3]dioxane-4,6-dione (160.2 g, 496 mmol) was dissolved in 800 mL of DOWTHERM A heat transfer fluid at 100° C. and added over 40 min by way of a cannula line to 1.3 L of preheated DOWTHERM A heat transfer fluid to 215° C. After complete addition, the reaction was held at 215° C. for 90 min and then cooled to RT. The resulting solid was collected by filtration, sequentially washed with diethyl ether (1.7 L) and acetone (500 mL), and then dried in a vacuum oven at 70° C. overnight. The resulting product (74.5 g) contained approximately 5% of the undesired isomer. This product was combined with material from a separate run (51.4 g) and slurried in 440 mL of refluxing ethanol. Filtration of the slurry while hot followed by sequential ethanol and diethyl ether rinses afforded 106.1 g of 7-phenylquinolin-4-ol as a tan solid.

出典