Water → HCID 22241639, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (5-benzyloxy-1H-indazol-3-yl)-acetic acid (2 g, 7.08 mmol) and sodium acetate (0.99 g, 12 mmol) in acetic anhydride (6 ml) was stirred at 130° C. for 3 h. After cooling, water (15 ml) and ethyl acetate (15 ml) were added to the reaction mixture. The aqueous layer was separated and extracted with ethyl acetate (2×15 ml). The combined extracts were washed with saturated aqueous NaHCO3 (2×20 ml) and saturated aqueous NaCl (20 ml), dried (MgSO4), and evaporated to a residue which was purified by chromatography (silica, 15% ethyl acetate in hexane) to give a yellow solid (0.48 g): 1H NMR (CD3OD) δ 8.35–8.30 (m, 1H), 7.48–7.23 (m, 6H), 7.04–7.02 (m, 2H), 5.11 (s, 2H), 4.02 (s, 2H), 2.77 (s, 3H), 2.27 (s, 3H); 13C NMR (CDCl3)δ 203.64 (C), 170.47 (C), 156.20 (C), 145.04 (C), 136.52 (C), 128.64 (CH), 128.31 (CH), 127.60 (CH), 120.51 (CH), 116.74 (CH), 102.26 (CH), 70.68 (CH2), 42.76 (CH2), 29.59 (CH3), 22.77 (CH3), MS(APCl) m/z 323 (M+H)+.

Provenance & Evidence