Sodium Chloride → N-[3-Hydroxy-1-(pyridin-3-yl)propyl]-4-methylbenzene-1-sulfonamide

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Reaction Steps

89.7 g (0.26 mole) of the sulfonamide was added to a suspension of 12.7 g (0.34 mole) of lithium aluminum tetrahydride in 1250 ml of dry glyme. The mixture was stirred and heated under reflux for 1.5 hours. A saturated sodium chloride solution was added at a temperature of from 0° to 5° C. and the mixture stirred and heated under reflux for 30 additional minutes. The insolubles were removed by filtration after standing overnight and the cake was washed with 200 ml of boiling glyme followed by two 250 ml aliquots of ethyl alcohol. The pH was adjusted to 7.8 with sodium bicarbonate and hydrogen chloride. Most of the glyme and alcohol were removed under reduced pressure and the resulting solid collected, washed with water and dried in a desiccator to yield 75.6 g (95.5% yield) of 3-(p-toluenesulfonamido)-3-(3-pyridyl)propanol.

Provenance & Evidence