1-Naphthalenecarbonitrile → HCID 14839218, compound

Participants

Reaction Steps

Part B. A solution of LDA in THF was prepared by the dropwise addition of 1.55M n-butyllithium in hexanes (130 mL, 202 mmol) to a solution of diisopropylamine (28.5 mL, 203 mmol) in THF (500 mL) at -78°. A solution of the product of Part A (30.00 g, 183.8 mmol) in THF (50 mL) was added dropwise at -78° to the LDA in THF solution, and the reaction mixture was stirred for one hour at -78°. A solution of 1-cyanonaphthalene (28.15 g, 183.8 mmol) in THF (50 mL) was then added dropwise to the reaction mixture at -78°, and after complete addition the reaction mixture was allowed to gradually warm to room temperature and stirred overnight. The reaction mixture was quenched with excess saturated aqueous NH4Cl and then most of the THF was removed by distillation under nitrogen. The resulting precipitate was filtered, washed with water, dried, and recrystallized from DMF-EtOH to afford the title compound (41.6 g, 153.3 mmol, 83% yield) as a white solid. The mother liquor was concentrated and the residue was recrystallized from DMF-EtOH to afford a second crop (5.6 g, 20.6 mmol, 11% yield) as a white solid: mp 225°-226°; IR(CHCl3) 1573 cm-1 ; MS m/e 272(M+ +H); 1H NMR(DMF-d7) δ 11.49(s,1H), 8.33(d,J=7.9 Hz,1H), 7.87-8.17(m,3H), 7.47-7.85(m,7), 6.72(s,1H). Anal. Calcd for C19H13NO: C,84.11; H,4.83; N,5.16. Found: C,83.90; H,4.70; N,5.12.

Provenance & Evidence