Sodium hydride → HCID 11554399, compound

Participants

Reaction Steps

A solution of 1-benzyl-1, 2, 3, 4-tetrahydro-quinolin-6-ol (0.239 g., 1 mmol) in dry tetrahydrofuran (5 ml) was added to a stirred suspension of sodium hydride (0.024 g., 1 mmol) in dry tetrahydrofuran (5 ml) at −10° C. during 5 min. The reaction mixture was stirred for 20 min. Then 4-chloro-3-trifluoromethyl-phenyl isocyanate (0.265 g., 1 mmol) was added to the stirring reaction mixture. Stirring was continued for additional 2.5 hours during which the temperature was allowed to rise to room temperature (34° C.). The reaction mixture was quenched with water (0.2 ml), concentrated under vaccum, diluted with water (5 ml), extracted with chloroform (2×5 ml) and dried over sodium sulphate. The combined fractions of chloroform were concentrated under vaccum. The residue was chromatographed on silica gel using chloroform-hexane (20:80) as eluant to give 2k; yield: 0.25 g. (54.2%), m.p. 151° C., C24H20ClF3N2O2; 1H NMR δ ppm (CDCl3): 2.00 (bs, 2H), 2.79 (t, 2H), 3.36 (t, 2H), 4.46 (s, 2H), 6.42-6.46 (m, 1H), 6.70-6.79 (m, 2H), 6.96 (s, 1H), 7.23-7.31 (m, 5H), 7.75-7.82 (m, 2H); IR vmax (KBr) (cm−1): 555, 701, 898, 1027, 1218, 1362, 1509, 1635, 1721, 2375, 2658, 2957, 3028, 3449, 3756; MS: m/z=461 (M+).

Provenance & Evidence