Synthesis
Acetic anhydride (120 μL, 1.0 eq.) was slowly added to a solution of 7-amino-2-naphthol (1.57 mmol) in dichloromethane (8 mL) under inert atmosphere. The reaction mixture was stirred at room temperature for 5 h. Acetic anhydride (240 μL, 2.0 eq.) was added again. The reaction mixture was continued to be stirred at room temperature for 16 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the resulting residue was purified by column chromatography after pre-adsorption on silica gel. The target compound 1-acetamido-7-naphthol (compound 12) was finally obtained as a brown solid in 88% yield. Mass spectrometry analysis showed M/Z(M + H)+ = 202.
References
[1] Patent: EP1961738, 2008, A1. Location in patent: Page/Page column 13
[2] Chemische Berichte, 1909, vol. 42, p. 352
[3] Chemische Berichte, 1896, vol. 29, p. 41
[4] Journal of Medicinal Chemistry, 2005, vol. 48, # 12, p. 3953 - 3979
[5] Journal of Organic Chemistry, 2005, vol. 70, # 24, p. 10004 - 10012
