Sodium Hydroxide → 5-(Hexyl{4-[(4-methoxyphenyl)ethynyl]benzyl}amino)-2-hydroxybenzoic acid

Participants

Reaction Steps

To a solution of 6-(hexyl{4-[(4-methoxyphenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-one (520 mg; 1.05 mmol) in MeOH (20 mL) was added an aqueous solution of NaOH (1.05 mL, 5N). The reaction mixture was stirred at rt for 1 h. The yellow precipitate obtained was filtrated and washed with cola water. It was suspended again in MeOH (20 mL) and aqueous solution of NaOH (2 mL, 5N) and heated at 70° C. overnight. The reaction mixture was poured into an aqueous solution of HCl (1N) and extracted with Et2O. The combined organic layers were washed with brine, dried over magnesium sulfate, filtrated and concentrated. Purification by preparative HPLC using a X-Terra column followed by a recrystallisation in MeOH gave 55 mg (12%) the title compound as a brown powder. HPLC, Rt: 4.24 min purity: 95.0%). LC/MS, M+(ESI): 458.3, M−(ESI): 456.1 1H NMR (CDCl3) δ: 12.70 (brs, 1H), 10.20 (brs, 1H), 7.46 (d, J=5.3 Hz, 2H), 7.44 (d, J=4.5 Hz, 2H), 7.23 (d, J=7.3 Hz, 2H), 6.98 (m, 4H), 6.78 (d, J=9.0 Hz, 1H), 4.46 (s, 2H), 3.78 (s, 3H), 3.31 (m, 2H), 1.51 (m, 2H), 1.25 (m, 6H), 0.84 (m, 3H).

Provenance & Evidence