Succinic anhydride → HCID 67691185, compound

Participants

Reaction Steps

To a suspension of trans-2-methoxycarbonyl-5,7-dichloro-4-amino-1,2,3,4-tetrahydroquinoline hydrochloride (Example 9a) (225 mg, 0.819 mmol) in ethyl acetate (50 ml) was added a solution of potassium carbonate (50 ml). The mixture was shaken until no solid remained (5 min). The organic layer was retained and washed with brine (50 ml) before drying (Na2SO4). The solvent was removed in vacuo. The residue was redissolved in xylene (20 ml) and succinic anhydride (90 mg, 0.901 mmol) was added. The mixture was heated, with stirring, in an oil bath (80° C.) for 16h. The precipitate was removed by filtration and washed with ether to give the title compound as a colourless crystalline solid. δ (DMSO, 250 MHz), 1.65 (1H, ddd, J=13.0, 12.7 and 3.7 Hz, CHACHBHCCHD), 2.15 (1H, dm, J=13.0 Hz, CHACHBHCCHD), 2.18-2.41 (4H, m, CO(CH2)2CO), 3.73 (3H, s, CH3), 3.94 (1H, dd, J 13.0 and 3.0 Hz, CHACHBHCCHd), 5.01 (1H, m, CHACHBHCCHD), 6.69 (1H, J=2.1 Hz, 6-H or 8-H), 6.86 (1H, d, J=2.1 Hz, 6-H or 8-H), 6.91 (1H, s, ArNHCH), 8.23 (1H, d, J=7.2 Hz, NHCO).

Provenance & Evidence