Quinoline → HCID 9971844, compound

Participants

Reaction Steps

The quinolinium salt/quinoline mixture was prepared from 3-acetyl-pyridine (440 μL, 4.00 mmol), quinoline (5.0 mL, 42 mmol) and iodine (1.02 g, 4.00 mmol) similar to Example 14, and yielded 312 mg of a brownish-green solid. The title compound was prepared from the quinolinium salt/quinoline mixture (290 mg), tetrapyridinecobalt(II) dichromate (346 mg, 0.568 mmol), sodium bicarbonate (131 mg, 1.56 mmol), acrylonitrile (180 μL, 2.73 mmol), and N,N-dimethylformamide (2.0 mL) similar to Example 14, yielded 15.5 mg (1.3% over 2 steps) as a yellow solid. 1H NMR (CDCl3): 8.80 (ddd, J=4.12, 1.65, 0.96 Hz, 1H), 8.24 (d, J=7.97 Hz, 1H), 8.12 (d, J=8.52 Hz, 1H), 7.99 (td, J=7.76, 1.83 Hz, 1H), 7.85 (m, 2H), 7.76 (d, J=9.07 Hz, 1H), 7.69 (d, J=9.06 Hz, 1H), 7.52–7.65 (m, 3H).

Provenance & Evidence