Quinoline → HCID 69414064, compound

Participants

Reaction Steps

5% Pd/CaCO3 poisoned with lead (Lindlar's catalyst) (1.37 g, 0.642 mmol) was added to a solution of (104) (2.17 g, 6.42 mmol) and quinoline (3.5 mL) in benzene (200 mL). The reaction flask was evacuated, and then backfilled with H2 from a balloon. The reaction was stirred under H2 for 2 h. (The reaction can be monitored by the 1HNMR of small aliquots which have been filtered through celite and concentrated, observing the disappearance of the alkyne proton or the appearance of the olefin protons.) After 2 h, more Pd catalyst was added (0.5 g) and the reaction was stirred 1.5 h more under H2. The reaction was filtered through a pad of celite, washed with EtOAc (300 mL) and concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (100 mL), washed with 2M HCl (4×200 mL) and sat. NaHCO3, dried (Na2SO4), and concentrated under reduced pressure to yield 1.65 g (76%) of a yellow solid. (LH-63-17)

Provenance & Evidence