Hydrochloric Acid → HCID 53789174, compound

Participants

Reaction Steps

To a solution of the product of Example 3H (3.36 g, 10.0 mmol) in dimethylformamide (10 mL) was added sodium chloride (586 mg, 10.0 mmol), water (360 microliters, 20 mmol) and 4N hydrochloride acid in dioxane (0.012 mL, 0.5 mmol). The reaction vessel was Firestone purged three times and placed under a positive nitrogen pressure. The reaction mixture was heated at reflux for 24 hours and then concentrated in vacuo. The residue obtained was diluted with water (5 mL) and extracted with ether (3×15 mL). The combined organic extracts were decolorized with charcoal (0.5 g), dried over magnesium sulfate, filtered, and concentrated in vacuo to afford the title product (2.51 g, 95%) as a pale yellow oil. 1H NMR (300 MHz, CDCl3) 1.29 (t, 3H), 2.04 (s, 3H), 2.99 (m, 2H), 4.22 (q, 2H), 4.79 (m, 1H), 5.53 (d, 1H), 5.68 (m, 1H), 6.44 (d, 1H); IR (film) 1195, 1220, 1370, 1540, 1660, 1740, 2990, 3050, and 3300 cm-1. MS (DCI/NH3) m/e 264/266 (M+H)+, 281/283 (M+H+NH3)+. Anal. Calcd. for C9H14NO3Br: C, 40.92; H, 5.34; N, 5.30. Found: C, 42.04; N, 5.48; N, 5.26.

Provenance & Evidence