Pyridine → 2-(p-Methoxybenzyloxy)acetic acid hydrazide

반응식

O.[NH2:2][NH2:3].N1C=CC=CC=1.C[O:11][C:12](=O)[CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1>C(O)C>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][O:14][CH2:13][C:12]([NH:2][NH2:3])=[O:11])=[CH:17][CH:18]=1

참가 물질

실험 절차

Add hydrazine hydrate (2.1 mL, 42.1 mmol) and pyridine (0.3 mL, 3.8 mmol) to a solution of (4-methoxy-benzyloxy)-acetic acid methyl ester (8.05 g, 38.3 mmol) in ethanol (100 mL, absolute). Heat the reaction to reflux under N2 overnight. Concentrate; add toluene and concentrate (2 times). Purify the residue by flash chromatography on silica gel eluting with 0-40% ACN/CH2Cl2 to afford the title compound (6.42 g, 80%) as clear oil. 1H NMR (400 MHz, DMSO) δ 3.73 (s, 3H); 3.84 (s, 2H); 4.24 (bs, 2H); 4.42 (s, 2H); 6.89 (d, 2H, J=8.3 Hz); 7.27 (d, 2H, J=8.3 Hz); 9.00 (bs, 1H). MS(IS) 209 (M−).