Iodine → 2-iodo-5-propoxy-4H-benzo[f]quinolin-1-one

HRID 1474519Notes

Reaction equation

HRID 1474519 reaction equation
[CH2:1]([O:4][C:5]1[C:14]2[NH:13][CH:12]=[CH:11][C:10](=[O:15])[C:9]=2[C:8]2[CH:16]=[CH:17][CH:18]=[CH:19][C:7]=2[CH:6]=1)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].[I:26]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C.C(OCC)(=O)C>[I:26][C:11]1[C:10](=[O:15])[C:9]2[C:8]3[CH:16]=[CH:17][CH:18]=[CH:19][C:7]=3[CH:6]=[C:5]([O:4][CH2:1][CH2:2][CH3:3])[C:14]=2[NH:13][CH:12]=1

Participants

7

Reactant 4

HCID 807IodineHCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 584923735-propoxy-4H-benzo[f]quinolin-1-one

Product 1

HCID 584923712-iodo-5-propoxy-4H-benzo[f]quinolin-1-oneYield 87.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Propoxy-4H-benzo[f]quinolin-1-one (2.66 g, 10.5 mmol) was suspended in DMF (20 ml). Potassium carbonate (1.63 g, 11.8 mmol) and iodine (2.95 g, 11.6 mmol) were added to the suspension, followed by stirring at room temperature for 3 hours. The reaction mixture was poured into an aqueous sodium thiosulfate solution (9.14 g, 100 ml), followed by stirring for 5 minutes. Ethyl acetate was added to the reaction mixture and stirred. Subsequently, insoluble matter was collected by filtration, and the filtrate was then separated. The thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution, and then concentrated to dryness under reduced pressure. The residue was added to the collected insoluble matter, followed by purification using silica gel column chromatography (dichloromethane:methanol=50:1→20:1). The purified product was concentrated to dryness under reduced pressure, giving a pale brown powder of 2-iodo-5-propoxy-4H-benzo[f]quinolin-1-one (3.48 g, yield: 87%).

Workup

  1. stirringby stirring for 5 minutes
  2. stirringstirred
  3. filtrationSubsequently, insoluble matter was collected by filtration
  4. customthe filtrate was then separated
  5. washThe thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution
  6. concentrationconcentrated to dryness under reduced pressure
  7. additionThe residue was added to the collected insoluble matter
  8. customfollowed by purification
  9. concentrationThe purified product was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-d3964bb00dcd4226bbc83100a6d76b55
Source dataset
uspto-grants-2015_04
Patent number
US09018229B2

Reaction notes

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