1-Naphthalenecarbonitrile → HCID 14839227, compound

Participants

Reaction Steps

Part D. A solution of LDA in THF was prepared by the dropwise addition of 1.6M n-butyllithium in hexanes (17 mL, 27 mmol) to a solution of diisopropylamine (4.0 mL, 28.5 mmol) in THF (50 mL) at -78°. A solution of the product of Part C (5.00 g, 24.2 mmol) in THF (15 mL) was added dropwise to the LDA solution at -78° and the reaction mixture was stirred for one hour at -78°. A solution of 1-cyanonaphthalene (3.70 g, 24.2 mmol) in THF (15 mL) was 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 for 2 hours. The reaction mixture was quenched with excess saturated aqueous NH4Cl. The layers were separated and the aqueous phase was extracted with ether. The combined organic extracts were washed with saturated NaCl, dried, and concentrated. The residue was recrystallized from ethyl acetate to afford 7-(dimethylamino)-3-(1-naphthalenyl)-1(2H)-isoquinolinone (1.84 g, 5.85 mmol, 24% yield) as a solid. The mother liquor was concentrated and the residue was recrystallized from 6:4:0.5 hexane-ethyl acetate-methanol to afford a second crop (1.41 g, 4.48 mmol, 19% yield) as a solid: mp 205°-206°; IR(CHCl3) 1650 cm-1 ; HRMS m/e calcd for C21H18N 2 O (M+) 314.1419, found 314.1426; 1H NMR(CDCl3) δ 8.72(s,1H), 8.00-8.17(m,1H), 7.83-8.00(m,2H), 7.38-7.70(m,6H), 7.10-7.29(m,1H), 6.63(s,1H), 3.10(s,6H). Anal. Calcd for C21H18N2O: C,80.23, H,5.77; N,8.91. Found: C,79.88; H,5.58; N,8.71.

Provenance & Evidence