Hydrochloric Acid → 1-Cyano-4-hydroxy-7-phenyl-isoquinoline-3-carboxylic acid methyl ester

Participants

Reaction Steps

A mixture of 4-hydroxy-7-phenyl-isoquinoline-3-carboxylic acid methyl ester (170 mg, 0.61 mmol) and bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate (783 mg, 1.52 mmol) in CH2Cl2 (10 mL) was stirred at r.t. for 16 h, then diluted with CH2Cl2 (50 mL). The resulting mixture was washed with 5% sodium thiosulfate and 1 M HCl. The organic layer was dried over MgSO4 and concentrated. To the residue were added CuCN (102 mg, 1.14 mmol) and anhydrous DMF (6 mL), and the resulting mixture was refluxed for 20 min. After cooling to r.t., the reaction mixture was poured into a mixture of CH2Cl2 (100 mL) and water (100 mL). 4 M HCl was added with vigorous stirring until no solid was observed. The aqueous layer was extracted with additional CH2Cl2, and the organic layers were combined, dried over MgSO4 and concentrated. The crude product was purified by column chromatography (20-100% CH2Cl2/hexanes) to give 93 mg of the title compound as a light brown solid. MS: (+) m/z 305.06 (M+1).

Provenance & Evidence