Methyl N-aminocarbamate Hydrochloride → methyl N-[(E)-[2-(4-methyl-2-pyridin-3-yl-1,3-thiazol-5-yl)-6,7-dihydro-5H-quinolin-8-ylidene]amino]carbamate

Participants

Reaction Conditions

Reaction Steps

A solution of 2-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-6,7-dihydro-5H-quinolin-8-one (0.030 g, 0.093 mmol), methyl N-aminocarbamate hydrochloride (0.018 g, 014 mmol)) and acetic acid (1drop) were dissolved in methanol (0.9 mL) at ambient temperature and the resulting orange solution was stirred at 75° C. for 1 hour: LC-MS after this time showed reaction completion. The mixture was diluted with ethyl acetate, and then washed successively with saturated aqueous NaHCO3 and then water. The organic phase was, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography eluting with 0%-10% Methanol: Dichlormethane gradient gave the title product (29 mg, 79%) as yellow-orange solid. mp: 194-200° C.

Provenance & Evidence