Diphenyl Ether → 7-Fluoro-1,5-naphthyridin-4-ol

HRID 2176656Notes

Reaction equation

HRID 2176656 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][CH:9]=[C:10]2[C:15](=[O:16])OC(C)(C)OC2=O)[CH:5]=[N:6][CH:7]=1.C1(OC2C=CC=CC=2)C=CC=CC=1>>[F:1][C:2]1[CH:3]=[C:4]2[C:5]([C:15](=[O:16])[CH:10]=[CH:9][NH:8]2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 7583Diphenyl EtherHCID 675034075-((5-Fluoropyridin-3-ylamino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 675043247-Fluoro-1,5-naphthyridin-4-olYield 45%

Conditions

Temperature
250 °C

Procedure

A 500 mL round bottom flask equipped with a reflux condenser was charged with 5-((5-fluoropyridin-3-ylamino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (8.0 g, 30.0 mmol) and diphenyl ether (83.5 mL). This was heated to 250° C. in heating mantle and allowed to stay at this temperature for five minutes. Cooled to room temperature, diluted with hot hexanes, and filtered to afford 7-fluoro-1,5-naphthyridin-4(1H)-one (2.2 g, 45% yield) as a crude brown solid. The title compound was used without further purification. MS [M+H]=165.2, Calc'd for C8H5FN2O=164.14.

Workup

  1. customA 500 mL round bottom flask equipped with a reflux condenser
  2. temperaturein heating mantle
  3. temperatureCooled to room temperature
  4. filtrationfiltered

Sources & evidence

ORD record
ord-8fd3f8c1906f46ed8681a69aeff4ed68
Source dataset
uspto-grants-2015_06
Patent number
US09066954B2

Reaction notes

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