Hydrochloric Acid → HCID 19356272, compound

Participants

Reaction Steps

To a magnetically stirred suspension of 60% sodium hydride (60% in mineral oil) (0.53 grams) in anhydrous tetrahydrofuran (20 ml) at 0° C. is added a solution of 4-amino-2,5-dichloropyridine (0.90 grams) in anhydrous tetrahydrofuran (20 ml). After stirring for 30 minutes at room temperature the reaction mixture is cooled to 0° C. and treated with a solution of 4-methoxy-3-(11-phenylundecyloxy)benzoyl chloride (2.30 grams) in tetrahydrofuran (20 ml). After stirring at room temperature for 16 hours the reaction mixture is poured into 50 ml of 1N hydrochloric acid and extracted with ethyl acetate. The combined organics are washed with 1N hydrochloric acid, water and brine and then dried over sodium sulfate and concentrated under reduced pressure. The resulting yellow solid is purified by column chromatography on a silica gel column using a ratio of 9:1 mixture of methylene chloride and ethyl acetate as eluent to give 1.9 grams of an off-white solid. MP 114-5° C.; MS m/z 543, 545; Anal. calcd for C30H36Cl2N2O3 : C, 66.29; H, 6.68; N, 5.15. Found: C, 6646; H, 6.61; N, 5.08

Provenance & Evidence