Thionyl Chloride → 6-(3-Bromopropyl)-5,6-dihydro-5,11-dioxo-3-nitro-11H-indeno[1,2-c]isoquinoline

Participants

Reaction Steps

Thionyl chloride (5 mL) was added to a solution of cis-4-carboxy-3,4-dihydro-N-(3-bromopropyl)-3-phenyl-7-nitro-1(2H)isoquinolone (8b) (1.000 g, 2.308 mmol) in benzene (50 mL). The reaction mixture was heated at reflux for 30 min, allowed to cool to room temperature, and concentrated. The residue was diluted with nitrobenzene (30 mL), chilled in an ice bath, and aluminum chloride (0.616 g, 4.616 mmol) was added. The reaction mixture was removed from the bath and heated at 100° C. for 1 h. Ice water (100 mL) was added and the solution was extracted with CHCl3 (3×100 mL). The combined organic layer was washed with sat NaHCO3 (3×50 mL), sat NaCl (50 mL) and dried over sodium sulfate. The solution was concentrated, hexanes (900 mL) were added, and liquid was decanted. The obtained solid was washed with hexanes (100 mL) and the liquid was again decanted. The crude solid was purified by flash column chromatography (SiO2), eluting with chloroform, to provide an orange solid (0.432 g, 45%): mp 258-260° C. (dec). IR (film) 1672, 1612, 1560, 1503, 1428, and 1337 cm−1; 1H NMR (CDCl3) δ 9.20 (d, J=2.4 Hz, 1 H), 8.89 (d, J=8.9 Hz, 1 H), 8.52 (dd, J=9.0 Hz and 2.4 Hz, 1 H), 7.92 (m, 1 H), 7.75 (m, 1 H), 7.57-7.52 (m, 2 H), 4.76 (m, 2 H), 3.70 (t, J=6.2 Hz, 2 H), 2.54 (m, 2 H); CIMS m/z (rel intensity) 413/415 (MH+, 100/82). Anal. (C19H13BrN2O4) C, H, N.

Provenance & Evidence