HCID 10737142, compound → HCID 10735084, compound

Participants

Reaction Steps

A solution of the above nitro compound (175 mg, 0.49 mmol) in benzene (30 mL) was hydrogenated over PtO2 (45 mg) at 50 psi for 1 h. Removal of the catalyst and solvent provided a solid which was recrystallised from i-Pr2O/petroleum ether to give 5-amino-1-(chloromethyl)-3-trifluoroacetyl-1,2-dihydro-3H-benz[e]indole (143 mg, 89%), mp 177° C. 1H NMR [(CD3)2SO] δ 8.11 (d, J=8.4 Hz, 1 H, H-6), 7.80 (d, J=8.3 Hz, 1 H, H-9), 7.60 (s, 1 H, H-4), 7.50 (t, J=7.7 Hz, 1 H, H-8), 7.35 (t, J=7.7 Hz, 1 H, H-7), 6.14 (s, 2 H, NH2), 4.45 (dd, J=11.0, 8.7 Hz, 1 H, H-2), 4.33 (d, J 11.2 Hz, 1 H, H-2), 4.24-4.16 (m, 1 H, H-1), 4.03 (dd, J=11.0, 3.0 Hz, 1 H, CHHCl), 3.84 (dd, J=11.0, 7.1 Hz, 1 H, CHHCl). Anal. Calculated for C15H12ClF3N2O: C, 54.8; H, 3.7; N, 8.5; Cl, 10.8. Found: C, 55.1; H, 3.4; N, 8.6; Cl, 10.7%.

Provenance & Evidence