Sodium Hydroxide → HCID 86597528, compound

Participants

Reaction Steps

4-(5-Chloro-2-methoxy-phenyl)-3-oxiranylmethylsulfanyl-6-trifluoromethyl-4a,8a-dihydro-1H-quinolin-2-one (VIII) was prepared by alkylation of 4-(5-Chloro-2-methoxy-phenyl)-3-mercapto-6-trifluoromethyl-4a,8a-dihydro-1H-quinolin-2-one (Ie) with epibromohydrin. To a warm solution of Ie (2.6 mmol) and epibromohydrin (3.9 mmol) in abs. EtOH was added dropwise NaOH solution (1 Molar, 3.9 mL) forming a yellow solution. The alkylation was allowed to proceed at room temperature for an hour. The mixture was evaporated to dryness, redissolved into methylene chloride, washed with water and the organic layer dried over MgSO4. The desired product was purified by a silica-gel column eluted with mixtures of hexanes and ethyl acetate. The desired product (5) was obtained as an off-white solid in 70% yield, mp 211–212° C. Calcd. for C20H15Cl1F3N1O3S1: C, 54.34; H, 3.42; N, 3.17. Found: C, 54.35; H, 3.43, N, 3.01. 1H NMR (300 MHz, DMSO-d6) δ 7.94–7.83 (m, 2H), 7.64 (dt, J=9.0, 2.4 Hz, 1H), 7.39–7.32 (m, 3H), 5.27–5.21 (m, 1H), 4.53–4.51 (m, 1H), 3.99–3.66 (m, 4H), 3.26–3.24 (m, 1H), 3.12–3.02 (m, 1H).

Provenance & Evidence