Dimethyl Sulfate → 1-Methylquinolin-1-ium methyl sulfate

Participants

Reaction Steps

Pure, commercial grades of quinoline, benzene and dimethylsulfate were stored over Molecular Sieve 4A for two days prior to reaction. Into a three liter, three-necked round bottomed flask fitted with an electrical heater, stirrer, dropping funnel and an efficient reflux condenser equipped with calcium chloride drying tube were placed quinoline 300 ml. (328.8 g., 2.54 moles) in benzene 900 ml. Dimethyl sulfate 240 ml. (319.2 g., 2.53 moles) in benzene 180 ml. was run in rapidly over five minutes while the contents were vigorously stirred. Spontaneous warming and refluxing occurred and the liquid separated into two phases. After the initial reaction had subsided the flask was heated to reflux for two hours and then allowed to cool for two hours. All the time the reagents were vigorously stirred until the cooled mixture became a suspension of small particles. These were filtered as far as removing Cthe solvent, washed with benzene 1000 ml. and refiltered, and were transferred to tared bottles in a vacuum desiccator over sulfuric acid and sodium hydroxide. The desiccator was evacuated at room temperature for about six hours when no further benzene was collected in a liquid nitrogen trap. Total yield of dried material 633.5 g. (98%).

Provenance & Evidence