Sodium Hydroxide → HCID 22921568, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, 5.0 grams (0.026 mole) of N-(2-propyn-1-yl)-4-fluoro-2-nitroaniline in 250 mL of ethanol was added to 25.8 grams (0.114 mole) of stirred tin(II) chloride dihydrate. The reaction mixture was then warmed to 60° C. over a one hour period, after which 98% sodium borohydride pellets were added portionwise until thin layer chromatographic analysis of the reaction mixture indicated that the intermediate nitroaniline had been consumed. Consumption of the nitroaniline required about 2.0 grams (0.052 mole) of sodium borohydride. The reaction mixture was then cooled to about 10° C., and 50 mL of cold water, followed by 15 mL of cold aqueous 10% sodium hydroxide, was added dropwise. After this time, the reaction mixture was concentrated under reduced pressure to remove the majority of the ethanol solvent. The concentrate was extracted with four 75 mL portions of diethyl ether. The combined extracts were washed with aqueous 5% sodium hydroxide and then with an aqueous solution saturated with sodium chloride. The organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil, which was subjected to column chromatography on silica gel, with 1:3 ethyl acetate:hexane as the eluant. The product-containing fractions were combined and concentrated under reduced pressure, yielding 5.0 grams of 2-(2-propyn-1-ylamino)-5-fluoroaniline. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence