Diethylamine → Ethyl 6-((diethylamino)methyl)picolinate

Participants

Reaction Steps

To a suspension of ethyl 6-(chloromethyl)picolinate (200 mg, 1.00 mmol) and KI (166 mg, 1.00 mmol) in DMF was added N,N-diethyl amine (73 mg, 1.00 mmol) and K2CO3 (304 mg, 2.20 mmol). The reaction mixture was stirred at rt for 5 h. LC-MS indicated the presence of product. The solvent was evaporated under reduced pressure and the residue was partitioned between EtOAc (20 mL) and water (20 mL). The organic layer was washed with water (15 mL) and dried over Na2SO4. The solvent was evaporated under reduced pressure to give ethyl 6-((diethylamino)methyl)picolinate (150 mg, 64%) as an oil. LC-MS (ESI) m/z 237 (M+H)+.

Provenance & Evidence