Reaction #155310

Reaction equation

N-(3-Propoxynaphthalen-2-yl)acetamide

hydrochloric acid

sodium hydroxide

→

3-propoxynaphthalen-2-ylamine

Yield 100.0%

Solvents

ethanol

Conditions

Workup

1. 1
   Temperaturewhile heating
2. 2
   Temperatureunder reflux
3. 3
   Extractionfollowed by extraction
4. 4
   ConcentrationThe thus-obtained organic layer was concentrated to dryness under reduced pressure
5. 5
   Otherthe residue was then purified
6. 6
   ConcentrationThe purified product was concentrated to dryness under reduced pressure

Procedure

N-(3-Propoxynaphthalen-2-yl)acetamide (2.5 g, 10.2 mmol) was dissolved in ethanol (10 ml). Concentrated hydrochloric acid (5.2 ml) was added thereto, and the resulting mixture was stirred for 4 hours while heating under reflux. The reaction mixture was cooled to room temperature, and a 5N aqueous sodium hydroxide solution (12.5 ml) was added thereto to adjust its pH to 11, followed by extraction using dichloromethane. The thus-obtained organic layer was concentrated to dryness under reduced pressure, and the residue was then purified using silica gel column chromatography (dichloromethane). The purified product was concentrated to dryness under reduced pressure, giving a white powder of 3-propoxynaphthalen-2-ylamine (2.05 g, yield: 100%).

Source