Sodium Methoxide → HCID 67304654, compound

Participants

Reaction Steps

5-(3,3-Diethoxypropylamino)-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylic acid (432 g, 1.27 mol) was mixed with sodium methoxide (95% pure, 75.8 g, 1.33 mol) and suspended in xylenes (2 L). The resultant mixture was heated at reflux for 2 h. The reaction mixture was gradually cooled to room temperature with stirring to afford light brown solids. The solids were collected by filtration and washed with toluene and dried under vacuum at 50-60° C. for 48 h to give the desired intermediate sodium 5-(3,3-diethoxypropylamino)thieno[3,2-b]pyridin-7-olate (a solid). This crude product was used in the next step without further purification. 1H NMR (400 MHz, DMSO d6) δ 1.08 (m, 6H), 1.72 (q, 2H, J=6.8 Hz), 3.15 (m, 2H), 4.55 (t, 1H, J=6 Hz), 6.22 (s, 1H), 6.98 (d, 1H, J=5.2 Hz), 7.53 (d, 1H, J=5.2 Hz).

Provenance & Evidence