反応 #1106611

反応方程式

2-hydroxy-1-naphthaldehyde

ethanol

aniline

→

2-hydroxy-1-naphthylmethylidene aniline

反応条件

後処理

1. 1
   温度under heating
2. 2
   workup.WAITUpon being left at rest over night in a refrigerator
3. 3
   その他a crystal was formed
4. 4
   その他the resulting precipitation
5. 5
   ろ過was filtered by Kiriyama funnel
6. 6
   その他Drying under reduced pressure at 25° C. for 24 hours

実験手順

6.88 g (40.0 mmol) of 2-hydroxy-1-naphthaldehyde was dissolved in 10 ml ethanol under heating, and 3.72 g (20.0 mmol) of aniline was added. After stirring under reflux at 70° C. for 1 hour, completion of the reaction was confirmed by TLC. Upon being left at rest over night in a refrigerator, a crystal was formed, and the resulting precipitation was filtered by Kiriyama funnel. Drying under reduced pressure at 25° C. for 24 hours gave 2-hydroxy-1-naphthylmethylidene aniline (hereinafter, also referred to as “HNA”) as a yellow crystal (9.17 g, 93%). 0.99 g (4.00 mmol) of HNA was dissolved in 50 ml deaerated ethanol, and 50 ml of a deaerated ethanol solution of 0.40 g (2.00 mmol) of copper acetate monohydrate was added with stirring. Upon stirring under reflux at 70° C. for 1 hour, a precipitation was formed, and completion of the reaction was confirmed by TLC. The resulting precipitation was filtered by Kiriyama funnel, and washed sufficiently with ethanol. Drying under reduced pressure at 25° C. for 24 hours gave a crude product of a complex compound NACu of the following formula as a red-brown crystal (1.10 g, 98%). Further, a part of the resulting crystal was dissolved in tetrahydrofuran, and ethanol having a 4-fold volume thereof was added to deposit a crystal. This crystal was filtered and dried under reduced pressure to give a purified product of the complex compound NACu.

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