2-Methoxybenzaldehyde → HCID 178489342, compound

Participants

Reaction Conditions

Reaction Steps

o-Anisaldehyde (0.105 ml, 0.866 mmol) and 4-bromo-2-methyl-6-nitroaniline (0.2 g, 0.866 mmol) in EtOH (3.46 ml) were treated with solid sodium dithionite (0.535 g, 2.60 mmol) and the mixture was heated to 80° C. for 16 hours following the procedure of D. Yang et. al. (Synthesis 2005, 47-56). The reaction mixture was taken to dryness and partitioned between ethyl acetate and 2N NH4OH(aq). After the usual work-up the crude material was purified by silica gel chromatography (Biotage 25S, 20% -40% ethyl acetate in hexanes) to obtained 159 (0.217 g, 0.684 mmol, 79% yield) as yellow solid. LRMS (ESI): (calc.) 316.0 and 318.0 (found) 317.1 and 319.1 (MH)+.

Provenance & Evidence