Water → 2,3-Bis(4-fluorophenyl)-7-hydroxyquinoxaline-6-carboxylic acid

HRID 2205121Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=O)=[CH:4][CH:3]=1.[NH2:19][C:20]1[C:28]([NH2:29])=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[C:22]([OH:30])[CH:21]=1.O>CC(O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)=[N:29][C:28]3[C:20](=[CH:21][C:22]([OH:30])=[C:23]([C:24]([OH:26])=[O:25])[CH:27]=3)[N:19]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 1,2-bis(4-fluorophenyl)ethane-1,2-dione (175 mg, 0.71 mmol, 1.00 equiv) and 4,5-diamino-2-hydroxybenzoic acid (120 mg, 0.71 mmol, 1.00 equiv) in HOAc (3 mL) was allowed to react, with stifling, for 3 hrs while the temperature was maintained at 130° C. in an oil bath. The reaction solution was poured into 10 ml of H2O. The resulting solid was filtered and purified by prep-HPLC, yielding 50 mg (19%) of 2,3-bis(4-fluorophenyl)-7-hydroxyquinoxaline-6-carboxylic acid as a yellow solid.

Workup

customto react
filtrationThe resulting solid was filtered
custompurified by prep-HPLC,

Sources & evidence

ORD record: ord-408c69b5b9874542aaf4abadceefae28
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09370522B2

Reaction notes

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