Methanol → HCID 59441954, compound

Participants

Reaction Steps

{2-[4,4-dimethyl-6-(methyloxy)-7-nitro-3,4-dihydro-1(2H)-quinolinyl]-2-oxoethyl}dimethylamine (assumed 2.8 mmol) was dissolved in a mixture of ethyl acetate (50 mL) and water (5 mL) and transferred to a Fischer Porter apparatus. 10% Palladium on carbon (500 mg, Aldrich) was added followed by methanol (5 mL) and the mixture stirred under 60 psi hydrogen pressure for 2 h. The pressure was released, the reaction vessel evacuated, and back-filled with nitrogen twice. The mixture was filtered through celite and the filtrate was concentrated to provide 1-[(dimethylamino)acetyl]-4,4-dimethyl-6-(methyloxy)-1,2,3,4-tetrahydro-7-quinolinamine (724 mg, 2.49 mmol, 89% over three steps). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.20 (s, 6 H), 1.62-1.68 (m, 2 H), 2.20 (s, 6 H), 3.17 (s, 2 H), 3.62-3.69 (m, 2 H), 3.75 (s, 3 H), 4.58 (bs, 2 H), 6.56-6.94 (s at 6.71 on top of a very broad singlet caused by amide rotomers, 2 H); ESIMS (M+H)+=292.

Provenance & Evidence