Hydrochloric Acid → Formic acid N'-[3-(2-dimethylamino-ethyl)-1H-indol-5-ylmethyl]-hydrazide, dihydrochloride

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Reaction Steps

A solution of HCl in ether (49.1 ml of a 2.138 molar solution, 105 mmol) is added under a nitrogen atmosphere to a solution of formic acid N′-[3-(2-dimethylamino-ethyl)-1H-indol-5-ylmethyl]-hydrazide (Example 13; 26.03 g, 100 mmol) in THF (300 ml) within 10 minutes. The obtained thick suspension of the product is filtered, and the filter cake washed with THF (ca. 80 ml) and ether (ca. 100 ml). The product is dried over night to give 28.04 g (84%) of cream colored hygroscopic crystals. 1H-NMR (DMSO-D6, 300 Mhz) □ 2.81 (s, 6H, HN+(CH3)2); 3.13 (m, 2H, CH2); 3.30 (m, 2H, CH2); 4.05 (s, 2H, CH2N+); 7.10 (dd, 1H, J=8.3 Hz, J=1.7 Hz, H-6); 7.21 (d, J=2.6 Hz, H-2); 7.32 (d, 1H, H-7); 7.63 (d, 1H, H-4); 7.96 (s, 1H, CHO); 10.9-11.15 (brs, H+); 11.10 (d, 1H, NH).

Provenance & Evidence