Acetic Acid → HCID 783358, compound

Participants

Reaction Steps

To a solution of morpholine (2.8 mL, 32.3 mmol) in tetrahydrofuran (100 mL) is added 5-chloro-2-nitrobenzaldehyde (5 g, 26.9 mmol) followed by sodium triacetoxyborohydride (11.4 g, 53.9 mmol) and HOAc (3.2 mL, 53.9 mmol) and the reaction is stirred overnight. The reaction is poured into a saturated aqueous Na2CO3 solution and extracted with ethyl acetate. The combined extracts are washed with H2O, brine, dried (Na2SO4) and concentrated to afford a clear oil. The residue is taken up in 1N aqueous HCl and removed insoluble material by filtration. The filtrate is neutralized with 2M aqueous K2CO3 and partitioned into ethyl acetate. The organic layer is dried (Na2SO4) and concentrated to afford the title compound (5.1 g, 74%) as an oil.

Provenance & Evidence