Water → 8-(2-Fluoro-3,5-dimethoxy-phenyl)quinoxaline-5-carboxylic acid

HRID 2409686Notes

Reaction equation

[OH-:1].[K+].[F:3][C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([O:12][CH3:13])=[CH:6][C:5]=1[C:14]1[C:23]2[N:22]=[CH:21][CH:20]=[N:19][C:18]=2[C:17]([C:24]#N)=[CH:16][CH:15]=1.[OH2:26]>C(O)CO.CCOCC.O>[F:3][C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([O:12][CH3:13])=[CH:6][C:5]=1[C:14]1[C:23]2[N:22]=[CH:21][CH:20]=[N:19][C:18]=2[C:17]([C:24]([OH:26])=[O:1])=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A solution of KOH (2.95 g, 52.7 mmol, 10 equiv) in H2O (20 mL) was added to 8-(2-fluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carbonitrile (Step 94.2) (1.63 g mg, 5.3 mmol) in ethylene glycol (20 mL). The reaction mixture was stirred at 150° C. for 5 h, allowed to cool to rt, diluted with Et2O/H2O, and extracted with Et2O. The aqueous phase was acidified to pH 3 by addition of HCl. The resulting yellow solid was collected by vacuum filtration to provide 1.71 g of the title compound: ESI-MS: 329.1 [M+H]+; tR=4.18 min (System 1).

Workup

temperatureto cool to rt
extractionextracted with Et2O
additionThe aqueous phase was acidified to pH 3 by addition of HCl
filtrationThe resulting yellow solid was collected by vacuum filtration

Sources & evidence

ORD record: ord-7eff7896eba342a3a072ce9cebd89b54
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815901B2

Reaction notes

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