Reaction #155318

Reaction equation

Benzhydrylidene(5-methylbenzofuran-7-yl)amine

Hydrochloric acid

sodium hydroxide

→

5-methylbenzofuran-7-ylamine

Solvents

THF

Conditions

Workup

1. 1
   Extractionfollowed by extraction
2. 2
   WashThe extract was sequentially washed with an aqueous saturated sodium hydrogen solution
3. 3
   DryingThe organic layer was dried over magnesium sulfate
4. 4
   Concentrationconcentrated to dryness under reduced pressure
5. 5
   OtherThe residue was purified
6. 6
   ConcentrationThe purified product was concentrated to dryness under reduced pressure

Procedure

Benzhydrylidene(5-methylbenzofuran-7-yl)amine (17.9 g, 0.57 mmol) was dissolved in THF (150 ml). 5N Hydrochloric acid (50 ml) was added thereto, followed by stirring at room temperature for 2 hours. A 5N aqueous sodium hydroxide solution (40 ml) was added to the reaction mixture, followed by extraction using ethyl acetate. The extract was sequentially washed with an aqueous saturated sodium hydrogen solution and an aqueous saturated sodium chloride solution. The organic layer was dried over magnesium sulfate and concentrated to dryness under reduced pressure. The residue was purified using silica gel column chromatography (n-hexane:ethyl acetate=50:1→10:1). The purified product was concentrated to dryness under reduced pressure, giving a dark brown oily substance of 5-methylbenzofuran-7-ylamine (2.5 g, yield: 30%).

Source