1-Naphthalenecarbonitrile → HCID 14839223, 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 (111 mL, 166 mmol) to a solution of diisopropylamine (22.6 mL, 161 mmol) in THF (750 mL) at -78°. A solution of the product of Part A (29.13 g, 164.3 mmol) in THF (50 mL) was added dropwise to the LDA in THF solution at -78° and the reaction mixture was stirred for 1 hour at -78°. A solution of 1-cyanonaphthalene (25.2 g, 164.5 mmol) in THF (50 mL) was then added dropwise to the reaction mixture at -78°, and the reaction mixture was stirred at -78° for 1 hour after complete addition and then allowed to gradually warm with stirring to room temperature 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 hexane-ethyl acetate to afford the title compound (32.0 g, 112.1 mmol, 68% yield) as a solid: mp 221°-222°; MS m/e 286(M+ +H); IR(CHCl3) 1651 cm-1 ; 1H NMR(CDCl3) δ 8.70(s,1H), 8.23(s,1H), 7.83-8.13(m,3H), 7.40-7.73(m,6H), 6.67(s,1H), 2.53(s,3H). Anal. Calcd for C20H15NO: C,84.19; H,5.30; N,4.91. Found: C,83.93; H,5.03; N,4.79.

Provenance & Evidence