3-Nitrophenylboronic Acid → HCID 54174373, compound

Participants

Reaction Steps

5.0 g of 4-cyano-4-(3,4-dimethoxy-phenyl)-5-methyl hexanoic acid (0.0172 mol) and 2.32 g, 2.50 ml of N-methylphenethylamine (0.0172 mol) in the presence of 30 mg of 3-nitrophenylboronic acid (~1 mol %) were set to reflux in 80 mls of toluene. The formed water was removed by use of Dean and Stark apparatus. After overnight heating GC/MS analysis indicated complete conversion of the acid (RT=25.07 mins) to the amide (RT=38.33 mins, m/z 408). After allowing to cool, the toluene solution was washed with 100 ml of 1.0N NaOH solution. The basic aqueous layer was re-extracted with 100 ml of toluene. The organic layers were combined and washed with 100 ml of water. The organic layers were dried over MgSO4, filtered and evaporated to dryness giving the amide in essentially quantitative yield as a yellow/green coloured oil. IR (liq film) ν (C=0)=1649.9 cm-1.

Provenance & Evidence