Reaction #1106611

Reaction equation

2-hydroxy-1-naphthaldehyde

ethanol

aniline

→

2-hydroxy-1-naphthylmethylidene aniline

Conditions

Workup

1. 1
   Temperatureunder heating
2. 2
   workup.WAITUpon being left at rest over night in a refrigerator
3. 3
   Othera crystal was formed
4. 4
   Otherthe resulting precipitation
5. 5
   Filtrationwas filtered by Kiriyama funnel
6. 6
   OtherDrying under reduced pressure at 25° C. for 24 hours

Procedure

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.

Source