Dimethylformamide → HCID 22622309, compound

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Reaction Steps

A solution of ethyl 3-bromo-6-methoxy-1-naphthoate (Wrobel, et al; J. Med. Chem. 34, 2504 (1991) (206 mg, 0.66 mmol), Zn(CN)2, and tetrakis(triphenylphosphine) palladium (36 mg, 0.031 mmol) in DMF (12 mL) was stirred at 80° C. for 1 h. The mixture was diluted with DCM, washed with water, dried (MgSO4), filtered and concentrated to a yellow precipitate, and purified by chromatography (5% EtOAc in hexanes) to afford methyl 3-cyano-6-methoxy-1-naphthoate as a white powder (150 mg, 0.588 mmol, 88%). The ester was saponified by stirring in 2% water in THF with 1.5 equivalents of LiOH at 80° C. for 3 h to afford the title compound. 1H NMR (CDCl3) δ 8.99 (d, J=9.6, 1H), 8.33 (s, 1H), 7.45 (dd, J=9.3, 2.7, 1H), 7.26 (s, 1H), 7.22 (d, J=2.4, 1H).

Provenance & Evidence