Benzyl carbazate → HCID 68470517, compound

Participants

Reaction Steps

A 50 ml flask is charged with 3-(2-dimethylamino-ethyl)-1H-indole-5-carbaldehyde (Reference Example 9; 2.16 g, 10 mmol), hydrazinecarboxylic acid benzyl ester (1.66 g, 10 mmol), and methanol (30 ml). This mixture is heated at reflux over night, and then the solvent is removed on the rotavapor to leave the hydrazone as a foam. 1H-NMR (CDCl3, 300 MHz) δ 2.24 (s, 6H, N(CH3)2); 2.55, 2.81 (2 m, 2H each, CH2CH2NHMe2); 5.22 (s, 2H, OCH2); 6.86 (d, 1H, J=2 Hz, H-2); 7.09 (d, 1H, J=8.5 Hz, H-7); 7.23-7.36 (m, Ph-H); 7.43 (dd, 1H, J=1.5 Hz, H-6); 7.62 (d, 1H, H-4); 7.79 (br s, 1H, N═CH); 9.35 (br s, NH); 9.50 (s, 1H, H-1). 13C-NMR (CDCl3, 75 MHz) δ 23.57 (CH2); 45.36 (N(CH3)2); 60.26 (CH2NMe2); 67.47 (OCH2); 112.17 (C-7); 114.3 (C-3); 119.51 (C-4); 120.69 (C-6); 123.32 (C-2); 125.15 (C-5); 127.48 (C-9); 128.33, 128.50 (2C), 128.73 (2C), 136.40 (q) (Ph C); 137.76 (C-8) 147.50 (N═CH); 154.10 (NC═O).

Provenance & Evidence