Iodine → 4-Quinolinol, 3-iodo-

HRID 227130Notes

Reaction equation

HRID 227130 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH:3]=[CH:2]1.[OH-].[K+].[I:14]I>CN(C=O)C>[I:14][C:3]1[C:4](=[O:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[NH:1][CH:2]=1

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 691414-Hydroxyquinoline

Product 1

HCID 123768444-Quinolinol, 3-iodo-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1H-Quinolin-4-one (2.90 g, 20 mmol, 1 equiv) in 5 mL of DMF was treated with 1.12 g of KOH (2 equiv) and 5.30 g of iodine (1.05 equiv) for 2 hours. The reaction was quenched by slow addition of saturated aqueous solution of Na2S2O3. Filtration gave 3-iodo-1H-quinolin-4-one as an off-white solid.

Workup

  1. customThe reaction was quenched by slow addition of saturated aqueous solution of Na2S2O3
  2. filtrationFiltration

Sources & evidence

ORD record
ord-a663a3f815d4412d9d03fca6c3220b1e
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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