Reaktion #1147778

Reaktionsgleichung

diethyl 2-({4-[(acetyloxy)methyl]-2-iodoanilino}methylene)malonate

→

ethyl 6-[(acetyloxy)methyl]-4-hydroxy-8-iodo-3-quinolinecarboxylate

Ausbeute 62.2%

Lösungsmittel

Ph2O

—

hexanes

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting solid is collected
2. 2
   Sonstigedried
3. 3
   Sonstigechromatographed (Biotage flash 40S, gradient from CH2CI2 to 2% MeOH/CH2Cl2)
4. 4
   workup.ADDITIONProduct containing fractions
5. 5
   Einengenconcentrated

Vorschrift

A solution of diethyl 2-({4-[(acetyloxy)methyl]-2-iodoanilino}methylene)malonate (1.75 g) in Ph2O (20 mL) is heated at 250° C. for 40 min. The reaction is cooled to room temperature and diluted with hexanes. The resulting solid is collected and dried. The crude solid is adsorbed onto silica and chromatographed (Biotage flash 40S, gradient from CH2CI2 to 2% MeOH/CH2Cl2). Product containing fractions are combined and concentrated to yield 0.98 g (62%) of ethyl 6-[(acetyloxy)methyl]-4-hydroxy-8-iodo-3-quinolinecarboxylate, m.p. 119-123° C.

Quelle