Ethylene Glycol → 8-(3,5-Dimethoxy-phenyl)-quinoxaline-5-carboxylic acid

HRID 43044

Reaction equation

[OH-:1].[K+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:13]2[C:22]3[N:21]=[CH:20][CH:19]=[N:18][C:17]=3C(C#N)=[CH:15][CH:14]=2)[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1.[CH2:25]([OH:28])[CH2:26]O>CCOCC.O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:13]2[C:22]3[N:21]=[CH:20][CH:19]=[N:18][C:17]=3[C:26]([C:25]([OH:28])=[O:1])=[CH:15][CH:14]=2)[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1

Participants

Conditions

Temperature: 150 °C

Procedure

KOH (6.0 g, 107 mmol, 10 equiv) was added to 8-(3,5-dimethoxy-phenyl)-quinoxaline-5-carbonitrile (Step 1.3) (3.12 g, 10.7 mmol) in ethylene glycol (30 mL). The reaction mixture was stirred at 150° C. for 3 h (a solution was obtained), allowed to cool to rt, diluted with Et2O/H2O, and extracted with Et2O. The aqueous phase was acidified to pH 5 by addition of HCl. Vacuum filtration of the resulting suspension afforded 3.3 g of the title compound as a yellow solid: ESI-MS: 311.0 [M+H]+; tR=4.34 min (System 1).

Workup

customwas obtained),
temperatureto cool to rt
extractionextracted with Et2O
additionThe aqueous phase was acidified to pH 5 by addition of HCl
filtrationVacuum filtration of the resulting suspension

Sources & evidence

ORD record: ord-38ce25d16e14442dade8dbee01847460
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536175B2

Linked notes

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