Diphenyl Ether → HCID 178469501, compound

HRID 852981Notes

Reaction equation

HRID 852981 reaction equation
C(O[C:4](=[O:20])[C:5](=[CH:11][NH:12][C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.C1(OC2C=CC=CC=2)C=CC=CC=1>C(O)C>[CH2:9]([O:8][C:6]([C:5]1[CH:11]=[N:12][C:13]2[C:14]([C:4]=1[OH:20])=[CH:15][C:16]([Br:19])=[CH:17][CH:18]=2)=[O:7])[CH3:10]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 1591151Diethyl 2-((4-bromophenylamino)methylene)malonate

Product 1

HCID 178469501HCID 178469501, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

The solid 2-[(4-bromo-phenylamino)-methylene]-malonic acid diethyl ester (157 g, 458.8 mmol) was added to a hot diphenyl ether (260 g) and the mixture was heated to reflux for 5 h to afford a brown suspension. Then, the mixture was cooled to 100° C. and diluted with ethanol (˜200 mL). This suspension was refluxed for 10 min and then cooled to room temperature. The solids were collected by filtration and washed with diethyl ether. After drying in air, 132.59 g (97.6% yield) of 6-bromo-4-hydroxy-quinoline-3-carboxylic acid ethyl ester was isolated as a white solid: EI-HRMS m/e calcd for C8H6N2O (M+) 146.0480, found 146.0478.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 5 h
  3. customto afford a brown suspension
  4. temperatureThis suspension was refluxed for 10 min
  5. temperaturecooled to room temperature
  6. filtrationThe solids were collected by filtration
  7. washwashed with diethyl ether
  8. customAfter drying in air

Sources & evidence

ORD record
ord-fa3ace34ba8046bbb9d46ddafd87c01d
Source dataset
uspto-grants-2007_08
Patent number
US07253285B2

Reaction notes

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