Dichloromethane → HCID 131724535, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 5-oxo-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxylate (25.0 g, 97 mmol) in 400 mL of methylene chloride was added N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (46.1 g, 194 mmol) and trifluoroacetic acid (2.22 g, 19 mmol). The reaction mixture was stirred at 40° C. for 24 h. The reaction mixture was allowed to cool and was washed with sat'd aq. NaHCO3 and brine, dried (K2CO3) and concentrated in vacuo. The residue was purified by recrystallization from 4:1 hexane/ethyl acetate to afford 36.6 g (96%) of the title compound of Part B as an off white solid. 1H NMR (CDCl3) δ: 7.37-7.20 (m, 5H), 7.05-7.00 (m, 1H), 6.97-6.88 (m, 2H), 4.28-4.19 (m, 1H), 4.12-4.01 (m, 2H), 3.80-3.68 (m, 4H), 3.57 (ABq, 2H, JAB=10.2 Hz), 3.17 (app t, 1H, J=8.8 Hz), 2.85-2.77 (m, 2H), 2.49 (app t, 1H, J=9.5 Hz), 2.05-1.95 (m, 2H), 1.09 (t, 3H, J=7.0 Hz).

Provenance & Evidence