Diisobutylaluminumhydride → N,O-Dimethylhydroxylamine

Participants

Reaction Steps

To a solution of 3-bromo-N-methoxy-N-methylpyridine-2-carboxamide (3-2; 219 mg, 0.89 mmole) in dry THF (4 mL) was added diisobutylaluminum hydride (0.94 mL, 0.94 mmole, 1M solution in CH2Cl2) slowly at −78° C. After 3 hr the mixture was quenched with 1N HCl and stirred vigorously. After 4 hr the mixture was neutralized with 1M NaOH and extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated to give 3-bromopyridine-2-carboxaldehyde and its animal with N,O-dimethylhydroxylamine as a mixture which was used in the next step without purification.

Provenance & Evidence