Synthesis
General procedure for the synthesis of 7-hydroxy-2-naphthalenecarbonitrile from 7-methoxy-2-naphthalenecarbonitrile: A solution of boron tribromide (840 μL, 8.8 mmol) in dichloromethane (4 mL) was added slowly and dropwise to a solution of 7-methoxy-2-naphthalenecarbonitrile (646 mg, 3.53 mmol) in dichloromethane (6 mL) under nitrogen protection. The reaction mixture was stirred at room temperature for 30 hours. Upon completion of the reaction, the reaction was quenched by the slow addition of deionized water (~5 mL). The pH of the reaction mixture was adjusted to 7 with saturated sodium carbonate solution and subsequently extracted with dichloromethane. The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography with the eluent being a mixture of dichloromethane and methanol (gradient elution: 1% dichloromethane solution in methanol to 5% dichloromethane solution in methanol) to afford 7-hydroxy-2-naphthalenecarbonitrile as a white solid (477 mg, 80% yield). The result of high resolution mass spectrometry (EI) analysis: the calculated value of C11H7NO was 169.0528 and the measured value was 169.0527.
References
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[2] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 12, p. 1156 - 1160
[3] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 22, p. 7434 - 7445
[4] Patent: US2003/236270, 2003, A1. Location in patent: Page 39
[5] Journal of the American Chemical Society, 1994, vol. 116, # 23, p. 10593 - 10600
