To synthesize a Ugi adduct from phenanthrene-9-carboxaldehyde, 1-heptylamine, tert-butylisocyanide and crotonic acid in methanol using Ugi 4CR
Procedure
To a one gram vial, charged with methanol (1mL) heptylamine, phenanthrene-9-carboxaldehyde, crotonic acid and tert-butyl isonitrile (0.5mmol each) was added in that order. After each addition, the resulting solution was vortexed for 15 seconds (or more) and confirmed that a homogeneous solution had been obtained. The vial was capped tight and left at room temperature for 3 days. The solution formed solid upon moving it to another spot. The obtained solid was washed with methanol (3 x 500uL), centrifuged each time to obtain a white residue. The wet product was set under a high vac to remove the solvent.
Characterization amount: 118.5 mg
m.p. 179-181C
HNMR(50mg in 700uL CDCl3)
CNMR(50mg in 700uL CDCl3)
HRMS (FAB) [M+Na]
Nominal Mass (FAB) [M+H]
Nominal Mass (FAB) [M+Na]
IR (KBr)
Conclusion
A Ugi product was successfully synthesized in 50% yield.