Chloride → 6-(Isoquinolin-5-yl)naphthalene-1-carboxamide

Participants

Reaction Steps

6-(isoquinolin-5-yl)-1-naphthoic acid (0.86 mg, 0.29 mmol) was suspended in CH2Cl2 (2 mL) and oxallyl chloride (0.038 mL, 0.4 mmol) was added followed by a drop of DMF. Mixture was stirred at room temperature for 3 h and solvent was evaporated and residue dried under vacuum. The crude acid chloride was dissolved in a solution of NH3 in dioxane and was stirred at room temperature. Solvent was evaporated, a solution of aqueous NaHCO3 was added and the mixture was extracted with CH2Cl2 and then with ethyl acetate. Residue was purified by prep plate (5% MeOH/CH2Cl2) to give the title compound as a solid. MS (ESI pos. ion) m/z: 299. (M+H). Calc'd Exact Mass for C20H14N2O: 298.

Provenance & Evidence