Pyridine → Methyl 4-acetamidosalicylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 10 g (59.9 mmol) of methyl 4-aminosalicylate in 100 ml of CH2Cl2 is added 6.8 ml (83.9 mmol) of pyridine in one portion at room temperature. The solution is cooled to 0° C. and 4.7 ml (65.9 mmol) of acetyl chloride is added dropwise. After addition is complete the reaction mixture is let stand 30 minutes at room temperature. The reaction mixture is diluted with water and extracted with CH2Cl2. The combined organic extracts are dried over MgSO4, filtered and concentrated to provide methyl 4-acetylaminosalicylate which is used directly in the next step.

Provenance & Evidence