Iodine → Ethyl 4,5-dihydroxyquinoline-3-carboxylate

HRID 423728Notes

Reaction equation

HRID 423728 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:13](=[O:17])[CH2:12][CH2:11][CH2:10][C:9]=2[NH:8][CH:7]=1)=[O:5])[CH3:2].II>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[OH:17])[NH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 807IodineHCID 12876362Ethyl 4,5-dioxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

Product 1

HCID 12956450Ethyl 4,5-dihydroxyquinoline-3-carboxylateYield 44.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4,5-dioxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester (1.6 g, 6.8 mmol) in ethanol (100 mL) was added iodine (4.8 g, 19 mmol). The mixture was refluxed for 19 h and then concentrated under reduced pressure. The resulting solid was washed with ethyl acetate, water and acetone, and then recrystallized from DMF to give 5-hydroxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester (700 mg, 43%).

Workup

  1. temperatureThe mixture was refluxed for 19 h
  2. concentrationconcentrated under reduced pressure
  3. washThe resulting solid was washed with ethyl acetate, water and acetone
  4. customrecrystallized from DMF

Sources & evidence

ORD record
ord-9e170cbbce724f00821fe31b98772f09
Source dataset
uspto-grants-2012_01
Patent number
US08101767B2

Reaction notes

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