Water → HCID 11371354, Verbindung

Beteiligte Stoffe

Reaktionsschritte

A suspension of racemic-(trans)-2-(4-aminophenyl)cyclopropanecarboxylic acid (I-1) (0.30 g, 1.69 mmol) and 4-(2-pyridinyl)benzaldehyde (0.37 g, 2.03 mmol) in dichloroethane (10 mL) were heated to reflux until a clear solution formed. The solution was cooled to RT then NaB(OAc)3H (0.54 g, 2.54 mmol) was added and stirred for 2 h. Water (50 mL) and dichloromethane (50 mL) were added and the organic layer was separated, dried over Na2SO4, filtered and concentrated. The crude material was purified on silica gel eluting with an increasing gradient from 20% ethyl acetate/hexanes to 100% ethyl acetate to give the title compound as a white solid (0.13 g, 22%). 1H NMR (400 MHz, DMSO) δ 12.15 (s, 1H), 8.65 (d, J=4.1 Hz, 1H), 8.02 (d, J=8.3 Hz, 2H), 7.92 (d, J=8.2 Hz, 1H), 7.86 (t, J=8.0 Hz, 1H), 7.44 (d, J=8.1 Hz, 2H), 7.32 (dd, J=5.2, 6.6 Hz, 1H), 6.84 (d, J=8.4 Hz, 2H), 6.50 (d, J=8.4 Hz, 2H), 6.23 (s, 1H), 4.30 (d, J=4.6 Hz, 2H), 2.22-2.17 (m, 1H), 1.61-1.57 (m, 1H), 1.31-1.27 (m, 1H), 1.20-1.16 (m, 1H).

Herkunft & Nachweise