Diphenyl Ether → Ethyl 6-iodo-4-oxo-1,4-dihydro-3-quinolinecarboxylate

HRID 230836Notes

Reaction equation

HRID 230836 reaction equation
C1(OC2C=CC=CC=2)C=CC=CC=1.[I:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][CH:22]=[C:23]([C:29]([O:31]CC)=O)[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:17][CH:16]=1>CC(CCC)C>[I:14][C:15]1[CH:16]=[C:17]2[C:18](=[CH:19][CH:20]=1)[NH:21][CH:22]=[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:29]2=[O:31]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 4026452Diethyl 2-((4-iodophenylamino)methylene)malonate

Product 1

HCID 719682Ethyl 6-iodo-4-oxo-1,4-dihydro-3-quinolinecarboxylate

Reagents, catalysts & solvents 1

HCID 78922-MethylpentaneSolvent

Procedure

Diphenyl ether (175 ml) was heated to reflux temperature, and Intermediate 10 was gradually added down an air condenser. Once all the reagent had been added the mixture was heated under reflux for a further 30 min. The mixture was then cooled and 2-methylpentane (200 ml) was added. The solid formed was collected by filtration to give the title compound (24.6 g).

Workup

  1. additionwas gradually added down an air condenser
  2. additionOnce all the reagent had been added the mixture
  3. temperaturewas heated
  4. temperatureunder reflux for a further 30 min
  5. temperatureThe mixture was then cooled
  6. customThe solid formed
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-54a385256a874b199dd6d9b03ea3d8d9
Source dataset
uspto-grants-2009_07
Patent number
US07566786B2

Reaction notes

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