Diphenyl Ether → 5-fluoro-8-propoxy-1H-quinolin-4-one

HRID 2167461Notes

Reaction equation

HRID 2167461 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][CH2:22][CH3:23])=[C:6]([NH:8][CH:9]=[C:10]2[C:15](=[O:16])OC(C)(C)OC2=O)[CH:7]=1.C1(OC2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>CCCCCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][CH2:22][CH3:23])=[C:6]2[C:7]=1[C:15](=[O:16])[CH:10]=[CH:9][NH:8]2

Participants

5

Reactant 3

HCID 7583Diphenyl EtherHCID 8857Ethyl AcetateHCID 669172145-[(5-Fluoro-2-propoxyphenylamino)methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione

Product 1

HCID 669172205-fluoro-8-propoxy-1H-quinolin-4-oneYield 61%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

5-[(5-Fluoro-2-propoxyphenylamino)methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione (7.6 g, 23.5 mmol) was added to diphenyl ether (15 ml), and the mixture was heated using a mantle heater, and then kept under reflux for 2 hours. After the reaction mixture was cooled to room temperature, ethyl acetate (5 ml) and n-hexane (10 ml) were added. The resulting mixture was stirred and the resultant insoluble matter was collected by filtration. The filtrate was recrystallized from an ethyl acetate-n-hexane mixed solvent to thereby obtain 3.15 g of powdery dark brown 5-fluoro-8-propoxy-1H-quinolin-4-one (yield: 61%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. filtrationthe resultant insoluble matter was collected by filtration
  4. customThe filtrate was recrystallized from an ethyl acetate-n-hexane mixed solvent

Sources & evidence

ORD record
ord-2a3b6321871f437b9baaebcded013094
Source dataset
uspto-grants-2015_06
Patent number
US09045464B2

Reaction notes

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