Reaction #1106614

Reaction equation

2-hydroxy-1-naphthaldehyde

ethanol

m-toluidine

→

2-hydroxy-1-naphthylmethylidene-3-methylaniline

Conditions

Workup

1. 1
   Temperatureunder heating
2. 2
   ConcentrationThe solution was concentrated with an evaporator to about 30 ml, whereupon a crystal
3. 3
   Otherwas formed
4. 4
   Filtrationwhich was filtered by Kiriyama funnel
5. 5
   OtherDrying under reduced pressure at 25° C. for 24 hours

Procedure

3.44 g (20.0 mmol) of 2-hydroxy-1-naphthaldehyde was dissolved in 50 ml ethanol under heating, and 2.14 g (20.0 mmol) of m-toluidine was added. After stirring under reflux at 70° C. for 1 hour, completion of the reaction was confirmed by TLC. The solution was concentrated with an evaporator to about 30 ml, whereupon a crystal was formed, which was filtered by Kiriyama funnel. Drying under reduced pressure at 25° C. for 24 hours gave 2-hydroxy-1-naphthylmethylidene-3-methylaniline (hereinafter, also referred to as “HNMT”) as a yellow crystal (4.43 g, 85%).

Source