Hydrochloric Acid → HCID 68546459, compound

Participants

Reaction Steps

7.5 g (23.71 mmol) N-(2,6-dimethoxybenzyl)-2-nitrobenzamide was dissolved in 130 mL THF, then 9.06 g boron-dimethyl sulfide-complex (2M solution in THF) was added by drops and the mixture was refluxed for 5 hours. Next 50 mL 2N HCl was added and the mixture was heated again at reflux for 30 minutes. For workup, the mixture was poured into water after cooling, a pH of approx. 10 was adjusted by adding 2N NaOH, further extraction was performed with ethyl acetate and the combined organic phases were dried with MgSO4. The crude product obtained by chromatography on silica gel (dichloromethane, 0-5% methanol) after filtration and evaporation yielded the desired amine; 3.58 g as a light yellow oil. ESI-MS [M+H+]=302.15.

Provenance & Evidence