Sulfuric Acid → Tert-Butylamine

Participants

Reaction Conditions

Reaction Steps

A mixture of the N-tert-butyl-2-(4-chlorophenyl)-6-(diethoxymethyl)-3-fluoropyridin-4-amine (130 mg, 0.34 mmol) in CH3CN (1 mL) and H2O (1 mL) was treated with 1 M H2SO4 (0.5 mL) resulting in a light yellow solution. The reaction flask was placed in an oil bath and heated to 78° C. After 4 h, an aliquot of the reaction mixture was partitioned between EtOAc and 10% NaHCO3 and analyzed by HPLC. HPLC analysis showed that all of the starting material had been consumed and only a trace of the desired product formed (mainly aldehyde with t-butylamine still intact). After stirring for 20 h at 78° C., HPLC analysis still showed only a trace of the desired product (<2%). The reaction was stopped at this point.

Provenance & Evidence