HCID 277932, compound → HCID 68564990, compound

Participants

Reaction Steps

A solution of 3-amino-4-t-butylbenzoic acid (10 g) in anhydrous tetrahydrofuran (150 ml) was added dropwise to a suspension of lithium aluminium hydride (4.0 g) in anhydrous tetrahydrofuran (150 ml) over a period of 45 minutes. The mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with tetrahydrofuran (150 ml) and aqueous sodium hydroxide solution (15%) was added to the mixture while cooling in an ice bath in order to decompose the excess lithium aluminium hydride. The insoluble material was filtered off through Celite (trademark) and the solvent of the filtrate was evaporated under reduced pressure to afford the desired compound (8.41 g, Rf=0.55: thin layer chromatography on a silica gel plate using n-hexane:ethyl acetate=1:3 as the eluant).

Provenance & Evidence