Acetic Anhydride → 1-Methyl-1,2,3,4-tetrahydroquinoline-6-carbonitrile

Participants

Reaction Conditions

Reaction Steps

1-Methyl-1,2,3,4-tetrahydroquinoline-6-carbaldehyde oxime (8.0 g, ca. 42.0 mmol) and Ac2O (40 mL, 423.9 mmol, 10.1 eq) was mixed at room temperature then the mixture was heated to 110° C. and stirred for 4 h. The solvent was removed under reduced pressure then the residue was placed on ice (500 g). The resulting mixture was quenched with saturated aqueous NaHCO3 then extracted by CH2Cl2 (4×50 mL). The combined organic layers were dried over Na2SO4 then concentrated to give a crude product which was purified by flash column chromatography (0-25% EtOAc in hexanes) to afford the title compound (4.53 g, 26.3 mmol, 63% over two steps).

Provenance & Evidence