N-Methyl-m-anisidine → HCID 14742779, compound

Participants

Reaction Steps

A solution of 3-methoxy-N-methylaniline (9.8 g) and 2-chloro-3-oxooctanenitrile (6.2 g) in ethanol (25 mL) was heated at reflux for 17 hours then the solvent was removed under reduced pressure. The residue was dissolved in dichloromethane (100 mL) and washed with 1N hydrochloric acid (3×50 mL). The aqueous layers were backwashed in turn with dichloromethane (50 mL) and the combined organic layers were dried (K2CO3) and evaporated. The residual oil was purified by HPLC (diethyl ether-hexane; 3:7) to yield 6.42 g of 2-(3-methoxy-N-methylanilino)-3-oxooctanenitrile as an oil. The above material was dissolved in trifluoroacetic acid (15 mL) and the solution was allowed to stand overnight at ambient temperature. The solvent was then evaporated and the residue was partitioned between dichloromethane (100 mL) and 1N sodium hydroxide solution (100 mL). The dried (K2CO3) organic layer was evaporated and the residue was purified by HPLC (diethyl ether-hexane; 1:1) to give 3.2 g of 6-methoxy-1-methyl-3-pentyl-2-indolecarbonitrile as an oil.

Provenance & Evidence