Réaction #155308

Équation de réaction

Hydrochloric acid

3-amino-2-naphthol

sodium carbonate

acetyl chloride

→

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

Rendement 78.0%

Solvants

acetone

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was cooled in an ice-water bath
2. 2
   workup.WAITto stand at room temperature overnight
3. 3
   AutreThe generated insoluble matter was separated
4. 4
   Lavagewashed with water
5. 5
   Autredried

Mode opératoire

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