Quinoline → HCID 18707021, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-acetylamino-3-(4-benzyloxyphenyl)-4-ethylpyrrolo[2,1,5-cd]indolizine-1-carboxylic acid, copper powder (0.52 g), and 130 ml of freshly purified quinoline was heated to 200 ° C. for 2 hours in a nitrogen atmosphere. The copper catalyst was filtered off from the warm mixture. Ice (200 g) was added to the filtrates and the pH was adjusted to 1.5 by addition of a 6M hydrochloric acid solution. The resulting mixture was extracted with dichloromethane. The extract was washed with a 1M hydrochloric acid solution (2×300 ml) followed by a saturated sodium hydrogen carbonate solution (2×250 ml). The dried extract (magnesium sulfate) was evaporated and the residue chromatographed over silica gel with toluene/ethyl acetate (2:1) as eluent to yield 1.52 (64%) of the title compound. M.p. 211-13° C. 1H-NMR (DMSO-d6, 200 MHz) δ: 1.38 (t, 3H), 2.22 (s, 3H), 3.18 (q, 2H), 5.18 (s, 2H), 7.23 (d, 2H), 7.35-7.55 (m, 7H), 7.75 (d, 2H), 8.03 (d, 1H), 8.22 (d, 1H), 10.50 (s, 1H).

Provenance & Evidence