Diphenyl Ether → 5-propoxy-4H-benzo[f]quinolin-1-one

HRID 1474518Notes

Reaction equation

HRID 1474518 reaction equation
CC1(C)O[C:6](=[O:8])[C:5](=[CH:9][NH:10][C:11]2[C:20]([O:21][CH2:22][CH2:23][CH3:24])=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)C(=O)O1.C1(OC2C=CC=CC=2)C=CC=CC=1>>[CH2:22]([O:21][C:20]1[C:11]2[NH:10][CH:9]=[CH:5][C:6](=[O:8])[C:12]=2[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=2[CH:19]=1)[CH2:23][CH3:24]

Participants

3

Reactant 2

HCID 7583Diphenyl EtherHCID 584924632,2-Dimethyl-5-[(3-propoxynaphthalen-2-ylamino) methylene][1,3]dioxane-4,6-dione

Product 1

HCID 584923735-propoxy-4H-benzo[f]quinolin-1-oneYield 106.3%

Procedure

2,2-Dimethyl-5-[(3-propoxynaphthalen-2-ylamino) methylene][1,3]dioxane-4,6-dione (4.19 g, 11.7 mmol) was added to diphenyl ether (15 ml), and the mixture was heated with a mantle heater and then maintained under reflux for 2 hours. The mixture was cooled to room temperature and purified using silica gel column chromatography (dichloromethane:methanol=70:1→9:1). The purified product was concentrated to dryness under reduced pressure, giving a dark brown powder of 5-propoxy-4H-benzo[f]quinolin-1-one (3.15 g, yield: 61%).

Workup

  1. temperaturethe mixture was heated with a mantle heater
  2. temperaturemaintained
  3. temperatureunder reflux for 2 hours
  4. custompurified
  5. concentrationThe purified product was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-61016512ae5f48e29b8ffc302d0dfeb3
Source dataset
uspto-grants-2015_04
Patent number
US09018229B2

Reaction notes

Loading…