Sodium Hydroxide → HCID 136397847, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-cyanopyridine (1.0 g, 5.50 mmol) in EtOH (100.0 mL) was added a solution of NaOH (0.22 g, 5.50 mmol dissolved in 2.0 ml H2O) followed by addition of NH2OH.HCl (0.38 g, 5.50 mmol). The resulting solution was heated to 60-65° C. for 16 h. After the completion of reaction (TLC monitoring), the solvent was evaporated and the residue was acidified with 3% HCl solution (20.0 mL) and heated to 100° C. till a clear solution was obtained. The reaction mixture was then cooled to room temperature and extracted with DCM (2×50 mL) that was later on discarded. The aqueous layer was basified with aqueous NH3 till pH 8 and extracted with EtOAc (3×50 mL). The combined organics was dried (Na2SO4), filtered and concentrated to obtain the desired product (0.75 g, 64%). MS: 216.01 (M+H)+.

Provenance & Evidence