Reaction #71386

Reaction equation

KOH

8-(2,6-dichloro-3,5-dimethoxy-phenyl)-2-[(2-dimethylamino-ethyl)-methyl-amino]-quinoxaline-5-carbonitrile

H2O

→

title compound

8-(2,6-Dichloro-3,5-dimethoxy-phenyl)-2-[(2-dimethylamino-ethyl)-methyl-amino]-quinoxaline-5-carboxylic acid

Solvents

ethylene glycol

Et2O H2O

Conditions

Workup

1. 1
   Temperatureto cool to rt
2. 2
   Extractionextracted with Et2O
3. 3
   workup.ADDITIONThe aqueous phase was acidified to pH 5 by addition of 6 N HCl
4. 4
   FiltrationVacuum filtration of the resulting suspension

Procedure

A solution of KOH (268 mg, 4.79 mmol, 10 equiv) in H2O (2 mL) was added to 8-(2,6-dichloro-3,5-dimethoxy-phenyl)-2-[(2-dimethylamino-ethyl)-methyl-amino]-quinoxaline-5-carbonitrile (Step 85.2) (220 mg, 0.48 mmol) in ethylene glycol (2 mL). The reaction mixture was stirred at 150° C. for 48 h, allowed to cool to rt, diluted with Et2O/H2O, and extracted with Et2O. The aqueous phase was acidified to pH 5 by addition of 6 N HCl. Vacuum filtration of the resulting suspension afforded 450 mg of the title compound as an impure yellow solid, which was used without further purification: ESI-MS: 479.0/480.9 [M+H]+; tR=3.75 min (System 1).

Source