Diphenyl Ether → 6-Bromo-1,4-dihydroquinolin-4-one

HRID 852983Notes

Reaction equation

HRID 852983 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6](C(O)=O)=[C:5]2[OH:15].C1(OC2C=CC=CC=2)C=CC=CC=1>CO.C(OCC)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[OH:15]

Participants

5

Reactant 2

HCID 7583Diphenyl EtherHCID 178524706HCID 178524706, compound

Product 1

HCID 1785163796-Bromo-1,4-dihydroquinolin-4-oneYield 95.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

The solid 6-bromo-4-hydroxy-quinoline-3-carboxylic acid (102.59 g, 337.7 mmol) was added to hot diphenyl ether (508 g) and then the mixture was heated to reflux for 9 h to afford a light brown suspension. After cooling to room temperature, the mixture was diluted with methanol (20 mL) and diethyl ether (300 mL). Then, the solids were collected by filtration and washed with diethyl ether. After drying in air, 72.43 g (95% yield) of 6-bromo-quinolin-4-ol was isolated as a white solid: EI-HRMS m/e calcd for C9H6BrNO (M+) 222.9633, found 222.9630.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 9 h
  3. customto afford a light brown suspension
  4. filtrationThen, the solids were collected by filtration
  5. washwashed with diethyl ether
  6. customAfter drying in air

Sources & evidence

ORD record
ord-1e300bacd405441086d12f449fd46249
Source dataset
uspto-grants-2007_08
Patent number
US07253285B2

Reaction notes

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