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

HRID 1297605Notes

Reaction equation

HRID 1297605 reaction equation
C(O[C:4](=[O:20])[C:5](=[CH:11][NH:12][C:13]1[CH:18]=[CH:17][C:16]([I:19])=[CH:15][CH:14]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.C(O)C>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:9]([O:8][C:6]([C:5]1[C:4](=[O:20])[C:14]2[C:13](=[CH:18][CH:17]=[C:16]([I:19])[CH:15]=2)[NH:12][CH:11]=1)=[O:7])[CH3:10]

Participants

4

Reactant 2

HCID 702EthanolHCID 4026452Diethyl 2-((4-iodophenylamino)methylene)malonate

Product 1

HCID 719682Ethyl 6-iodo-4-oxo-1,4-dihydro-3-quinolinecarboxylateYield 83%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
240 °C

Procedure

A mixture of 2-[(4-iodo-phenylamino)-methylene]-malonic acid diethyl ester (81 g, 0.21 mol) in diphenylether (60 mL) was refluxed at 240° C. for 14 h. After cooling, ethanol was added and the mixture was heated to reflux for 3 h. After cooling, the solid was collected by filtration, washed with hexane and dried to obtain 6-iodo-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester (59 g, 83%) as a yellow solid.

Workup

  1. temperatureAfter cooling
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 3 h
  4. temperatureAfter cooling
  5. filtrationthe solid was collected by filtration
  6. washwashed with hexane
  7. customdried

Sources & evidence

ORD record
ord-7345f10e7b584a81839eeab66a8b537b
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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