Acetic Anhydride → HCID 57324321, compound

Participants

Reaction Steps

(+)-(6S)-5,6,7,8-Tetrahydro-6-((4-methoxyphenyl)methyl)-3-methylquinoline-N-oxide (3,48g 0.012 mol) in toluene (40 ml) was added slowly to refluxing acetic anhydride (18 ml) and the mixture stirred for a further 3 hours. After cooling overnight, the reaction mixture was concentrated under reduced pressure and dissolved in methanol. The resulting solution was treated with 5M KOH until it was basic and again concentrated under reduced pressure. The residue was dissolved in water (40 ml) and washed with chloroform (3×40 ml). The combined organic phases were washed with brine (1×40 rml), dried (MgSO4) and concentrated under reduced pressure to give an oil (3.98 g) which solidified on standing. The product (1.9 g) was chromatographed on silica gel eluting with ethyl acetate to give the title compound (0.21 g), [α]D25 =+115% (1% CHCl3) mp 105°-7° C.

Provenance & Evidence