Hydrochloric Acid → 5-[(6-Chloroquinolin-2-yl)oxy]-2-nitrobenzoic acid

HRID 358124Notes

Reaction equation

[K].[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([OH:13])[CH:7]=[CH:6]2.F[C:15]1[CH:16]=[CH:17][C:18]([N+:24]([O-:26])=[O:25])=[C:19]([CH:23]=1)[C:20]([O-:22])=[O:21].Cl>CS(C)=O.O>[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([O:13][C:15]1[CH:16]=[CH:17][C:18]([N+:24]([O-:26])=[O:25])=[C:19]([CH:23]=1)[C:20]([OH:22])=[O:21])[CH:7]=[CH:6]2

Participants

Conditions

Temperature: 100 °C

Procedure

A reactor is charged with 4.34 grams (0.02 mole) of the potassium salt of 6-chloro-2-hydroxyquinoline (Formula II Compound) in 25 milliliters of dimethylsulfoxide. To this mixture is added 4.46 grams (0.02 mole) of the potassium salt of 5-fluoro-2-nitrobenzoate (Formula III Compound). After stirring at about 100° C. for about 16 hours, the reaction mixture is poured into 200 milliliters of water and acidified with concentrated hydrochloric acid. Filtration and air drying affords 5-(6-chloro-2-quinolinoxy)-2-nitrobenzoic acid (Formula IV Compound).

Workup

filtrationFiltration and air
customdrying

Sources & evidence

ORD record: ord-1bb98feec2e642abb2db4d648a58ece2
Source dataset: uspto-grants-1984_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04464533

Reaction notes

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