Hydrazine → HCID 10456060, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 14 (1.17 g, 2.68 mmol), hydrazine (1 mL, 32 mmol), and Raney-Ni in 95% EtOH (75 mL) was heated at 55° C. Small portions of Raney-Ni and hydrazine were added until TLC indicated completion of the reaction (2.5 h). The reaction was filtered through celite, and the Raney-Ni was washed with hot MeOH. The combined filtrates were evaporated under reduced pressure to yield 15 in quantitative yield. Further purification was achieved by gravity column chromatography with CHCl3 :1% MeOH:2% NH3 :mp (15.2HCl) softens at 149° C. and melts at 223°-224° C.; [α]D25°C. +143.7° (c=0.45, 15.2HCl, MeOH); 1H NMR (15.2HCl, DMSO-d6) δ 1.9-2.0 (m, 4H, --CH2CH2 --), δ 2.82 (s, 3H, NCH3), δ 3.07-4.07 (complex, 6H, 3 --CH2N), δ 3.77 (d, J=16 Hz, 1H, ArCH2CO), δ 4.10 (d, J=16 Hz, 1H, ArCH2CO), δ 6.05 (d of d, J=12.5 Hz and 2.5 Hz, 1H, CH), δ 6.87 (br s, 2H, m-NH2C6H4), δ 6.92 (d, J=8 Hz, 1H, m-NH2C6H4), δ 7.26 (t, J=8 Hz, 1H, m-NH2C6H4), δ 7.29-7.31 (m, 1H, Cl2C6 H3 --), δ 7.55-7.59 (m, 2H, Cl2C6H3 --). MS (FAB) m/z 406.2. Anal. (C21H25N3OCl2.2HCl) calcd.: C 52.62, H 5.68, N 8.77, Cl 29.59; found: C 52.43, H 5.58, N 8.50, Cl 29.47.

Provenance & Evidence