An efficient protocol for palladium-catalyzed picolinamide directed C8-H alkoxycarbonylmethylation of 1-naphthylamine derivatives with α-chloroalkyl esters has been developed. The reaction exhibited a broad substrate scope and good functional group tolerance with high isolated yields. Note that α-chloroalkyl esters as a new type of alkylating reagent could be easily functionalized further due to their pending an ester group.