L-Lysine → HCID 86759189, compound

Participants

Reaction Steps

5 g (34.2 mmol) of L-lysine are dissolved in 100 ml of water in the presence of 1.4 g (1 eq) of sodium hydroxide and 8.6 g (3 eq) of sodium bicarbonate in a 250 ml three-necked flask equipped with a reflux condenser and a thermometer. A solution of 10.8 ml (3 eq) of 4-fluoronitrobenzene in 60 ml of ethanol is run into the mixture, which is brought to reflux (85°-90° C.) for 5 days. The cooled mixture is extracted with ethyl ether. The aqueous phase is acidified to pH˜3 with 5N hydrochloric acid. A gummy precipitate is formed, which precipitate is extracted with dichloromethane in the presence of a small amount of methanol. The organic phase is washed with water to neutrality, dried over sodium sulphate and then evaporated to give an orange-colored oil which crystallizes in the presence of ethyl ether. 11.7 g of a yellow crystalline product are obtained, i.e. a yield of 88%.

Provenance & Evidence