N'-[3-(2-Dimethylamino-ethyl)-1H-indol-5-ylmethylene]-hydrazine-carboxylic acid isobutyl ester → HCID 58882812, compound

Participants

Reaction Conditions

Reaction Steps

A 50 ml pressure vessel is charged with N′-[3-(2-Dimethylamino-ethyl)-1H-indol-5-ylmethylene]-hydrazinecarboxylic acid isobutyl ester (Example 10; 1.76 g, 5.33 mmol), ethanol (25 ml), and the catalyst (5% Pd/C type E-4522, 325 mg). The vessel is sealed, purged with argon (three times and hydrogen (three times), heated in an oil bath to 65° C., and then pressurized with hydrogen (78.4 bar). The stirrer is started (900 rpm), and the hydrogenation allowed to proceed for 21.5 hours. After cooling to ambient temperature the pressure vessel is vented, and the reaction mixture filtered over a pad of Hyflo to remove the catalyst. Removal of the solvent gives the product as a pale yellow residue, which is pure by NMR. 1H-NMR (CD3OD, 300 MHz) δ 0.81 (d, 6H, J=6.8 Hz, CH(CH3)2); 1.78 (m, 1H, CH(CH3)2); 2.27 (s, 6H, N(CH3)2); 2.61, 2.83 (2 m, 2H each, CH2CH2NHMe2); 3.74 (d, 2H, J=6.6 Hz, OCH2); 3.90 (s, 2H, CH2N); 6.95 (s, 1H, H-2); 7.02 (dd, 1H, J=8.3 Hz, J=1.5 Hz, H-6); 7.19 (d, 1H, H-7); 7.43 (s, 1H, H-4). 13C-NMR (CD3OD, 75 MHz) δ 19.70 (CH3); 24.46 (CH2); 29.71 (CHMe2); 45.65 (N(CH3)2); 57.89 (CH2N); 61.64 (CH2NMe2); 72.57 (OCH2); 112.64 (CH); 113.85 (C); 120.42 (CH); 124.06 (CH); 124.33 (CH); 128.89 (C); 129.09 (C); 138.13 (C); 160.03 (C═O).

Provenance & Evidence