Sodium Hydroxide → HCID 21354847, compound

Participants

Reaction Steps

N-[(4-isopropylphenyl)methylene]-2,2-dimethoxyethanamine (5.0 g) was added to hot concentrated sulfuric acid (50 ml) at 140° C. dropwise over a period of 10 min. The mixture was stirred at this temperature for additional 10 min and cooled to RT. The mixture was basified with an aqueous solution of NaOH and the product was extracted with MTBE (6×75 ml). The combined organic layers were dried (MgSO4) and evaporated under reduced pressure. The residue was purified by flash chromatography on silica (pet. ether/EtOAc 9/1) to afford the titled compound as a solid (200 mg, 15%). TLC—Chloroform/methanol: (9.5/0.5): Rf=0.55. 1H NMR (CDCl3, 400 MHz) δ 1.28 (6H, d), 3.10 (1H, m), 7.49 (1H, d), 7.53 (2H, m), 7.89 (1H, d), 8.49 (1H, d), 9.19 (1H, s).

Provenance & Evidence