Sodium hydride → N-Methyl-N-[4-picolyl]formamide

Participants

Reaction Steps

To a solution of 4-picolyl chloride-HCl (15 g, 91.4 mmol) and N-methylformamide (53.4 mL, 914 mmol) in 300 mL of TMF was added 80% NaH in mineral oil (5.48 g, 183 mmol). After stirring at rt for 18 h the mixture was quenched with ice water and partitioned between CH2 Cl2 and H2O. The organic extract was washed with aqueous NaCl and dried over MgSO4. The solvent was removed in vacuo, and the residue was purified by flash chromatography, eluting with 50:1 CH2 Cl2 /MeOH. The title compound was obtained as a pale yellow oil (10.5 g, 76%): ESMS (m/z): 151 (M+ +H).

Provenance & Evidence