Ammonium Chloride → HCID 9883507, compound

Participants

Reaction Steps

A solution of 2-(3-ethylphenyl)-2-adamantanecarbonitrile (265 mg, 1 mmol) and NH4Cl (107 mg, 2 mmol) in dry toluene (5 mL) under argon was treated dropwise with 2-M trimethylaluminium in toluene (1.0 mL, 2 mmol), refluxed for 12 h, cooled to room temperature and purified directly by chromatography [SiO2; EtOAc—MeOH (9:1)] to give the title compound (178 mg, 56%) as a white solid: mp >300° C.; IR νmax (Nujol)/cm−1 2921, 2855, 1669, 1454, 1377, 1089, 798, 744 and 704; NMR δH (400 MHz, DMSO-d6) 1.18 (3H, t, J 8.0 Hz), 1.55-1.69 (7H, m), 1.83 (5H, s), 2.60 (2H, q, J 8.0 Hz), 3.15 (2H, s), 7.10-7.17 (1H, m), 7.27-7.38 (3H, m) and 8.88 (4H, br s); Anal. Calcd for C19H27ClN2.0.35 H2O: C, 70.18; H, 8.59; N, 8.61. Found: C, 70.25; H, 8.41; N, 8.46.

Provenance & Evidence