Reaktion #51895

Reaktionsgleichung

ethyl 2-(hydroxymethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate

4-chlorobenzylamine

sodium methoxide

→

title compound

Ausbeute 69.6%

N-(4-chlorobenzyl)-2-(hydroxymethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Ausbeute 69.6%

Lösungsmittel

methanol

methanol

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeduring the reaction
2. 2
   Filtrationthe mixture was filtered
3. 3
   Waschenthe collected solid was washed with methanol
4. 4
   Sonstigedried in vacuo
5. 5
   Sonstigeleaving a white solid
6. 6
   Temperaturcooled to room temperature
7. 7
   Filtrationfiltered

Vorschrift

A solution of ethyl 2-(hydroxymethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate (627 mg, 2.23 mmol), 4-chlorobenzylamine (2.0 mL, 16.4 mmol), 0.5 M sodium methoxide in methanol (25 mL, 8.92 mmol) and methanol (10 mL) was stirred under nitrogen in a tightly capped 250 mL round bottom flask at 50° C. for 24 hours. The initial solution slowly dropped a thick white precipitate during the reaction. After cooling to room temperature, the mixture was filtered, and the collected solid was washed with methanol and dried in vacuo, leaving a white solid. The crude solid was suspended in boiling methanol (200 mL), cooled to room temperature, and filtered, to give the title compound as a white powder (585 mg).

Quelle