Reaction #155308

Reaction equation

Hydrochloric acid

3-amino-2-naphthol

sodium carbonate

acetyl chloride

→

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

Yield 78.0%

Solvents

acetone

Conditions

Workup

1. 1
   TemperatureThe mixture was cooled in an ice-water bath
2. 2
   workup.WAITto stand at room temperature overnight
3. 3
   OtherThe generated insoluble matter was separated
4. 4
   Washwashed with water
5. 5
   Otherdried

Procedure

An acetone solution (60 ml) of 3-amino-2-naphthol (5.0 g, 31.4 mmol) was added to an aqueous solution (20 ml) of sodium carbonate (4.77 g, 34.5 mmol). The mixture was cooled in an ice-water bath, and then acetyl chloride (2.27 ml, 32.0 mmol) was added to the mixture dropwise over 5 minutes. The resulting mixture was stirred at 0° C. for 4 hours and then allowed to stand at room temperature overnight. 2N Hydrochloric acid was added to the reaction mixture to adjust its pH to 3. The generated insoluble matter was separated, washed with water, and then dried, giving a white powder of N-(3-hydroxynaphthalen-2-yl)acetamide (4.9 g, yield: 78%).

Source