Tert-Butyl isocyanide → HCID 71187265, compound

Participants

Reaction Steps

Under argon, methyl 2-formyl-3,5-dimethoxybenzoate (200 mg, 0.89 mmol) and 2-amino-4-chloropyridine (115 mg, 0.89 mmol) were dissolved in methanol (5 ml), after 5 minutes of stirring at room temperature tert-butylisonitrile (89 mg, 1.07 mmol) was added and after a further 10 minutes of stirring at room temperature 4-toluenesulphonic acid monohydrate (8 mg, 0.05 mmol) was added. The resulting reaction mixture was then stirred at room temperature for 6 h and subsequently concentrated under reduced pressure and taken up in 4 ml of trifluoroacetic acid. The mixture obtained in this manner was stirred at 50° C. for 3 h and then concentrated again, ethanol and water were added to the resulting residue and the pH was then adjusted to 8 using saturated sodium bicarbonate solution. Drying and removal of the resulting precipitate by filtration gave 10-chloro-1,3-dimethoxypyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-one in the form of a light-yellow solid (70 mg, 22% of theory). 1H-NMR (400 MHz, d6-DMSO δ, ppm) 13.20 (br. s, 1H, NH), 8.83 (d, 1H), 8.02 (s, 1H), 7.49 (m, 1H), 7.39 (d, 1H), 7.15 (s, 1H), 4.10 (s, 3H), 3.96 (s, 3H).

Provenance & Evidence