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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1029120Generated: November 3, 2026

4-Fluorophenol → HCID 58167957, compound

https://huagongshe.com/reaction/1029120

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-FluorophenolHCID 9732—
ReactantPotassium CarbonateHCID 11430—
Reactant1-Chlorobenzo[C][1,8]naphthyridin-6(5H)-oneHCID 58168008—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
ProductHCID 58167957HCID 5816795721%

Reaction Conditions

Temperature100 °C

Reaction Steps

1-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (50 mg, 0.22 mmol), 4-fluorophenol (73 mg, 0.65 mmol), and potassium carbonate (150 mg, 1.08 mmol) were suspended in DMF (2 mL), and stirred overnight at 100° C. The reaction solution was cooled to room temperature, diluted with H2O, and the resulting precipitate was filtered. The precipitate was washed with H2O, and dried under vacuum to provide 149 (14 mg, 21% yield) as a tan solid. LC-MS (M+H=307, obsd.=307). 1H NMR (400 MHz, d6-DMSO): δ 12.15 (s, 1H), 9.05 (d, 1H), 8.42 (dd, 1H), 8.29 (d, 1H), 7.88 (dt, 1H), 7.71 (t, 1H), 7.40 (m, 4H), 6.52 (d, 1H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08735584B2
Source datasetuspto-grants-2014_05
ORD IDord-4f2f99b0414044acb08dcf623c9849d9
Source noteuspto-grants-2014_05