Sodium Chloride → 3-(2-Hydroxyethyl)-1-(2-methyl-4-nitrophenyl)pyridin-2(1H)-one

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Reaction Steps

At 20° C., over the course of 20 min, 56.8 g (348 mmol) of borane-dimethylaniline complex were added dropwise to a solution of 50 g (174 mmol) of [1-(2-methyl-4-nitrophenyl)-2-oxo-1,2-dihydropyridin-3-yl]acetic acid in 100 ml of 2-methyl-THF. The mixture was after-stirred for 16 h and diluted with 500 ml of dichloromethane. Over the course of 30 min, this mixture was metered into a solution of 50 g of sodium chloride in 500 ml of 1M hydrochloric acid. The mixture was after-stirred for 1 h and the organic phase was washed again with 500 ml of a solution of 50 g of sodium chloride in 500 ml of 1M hydrochloric acid. Washing with 500 ml of a saturated aqueous sodium hydrogen carbonate solution, drying over sodium sulphate and evaporation were carried out. 40 g (84%) of the desired alcohol were obtained.

Provenance & Evidence