Iodine → 6-Iodo-3,4-dihydroquinolin-2(1H)-one

HRID 6812

Reaction equation

HRID 6812 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]1=[O:11].[I:12]I>C(O)C.S([O-])([O-])(=O)=O.[Ag+].[Ag+]>[I:12][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[NH:1][C:2](=[O:11])[CH2:3][CH2:4]2

Participants

5

Reactant 2

HCID 807IodineHCID 64796Hydrocarbostyril

Product 1

HCID 220189516-Iodo-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 159865Silver sulfateCatalystHCID 702EthanolSolvent2×

Procedure

3,4-Dihydroquinolin-2(1H)-one (7.5 g; 51 mmol) and silver (I) sulfate (17.5 g; 56.1 mmol) were suspended in ethanol (250 mL). A solution of iodine in ethanol (250 mL) was added slowly to the reaction over 1 hour. After 6 hours, the reaction was filtered through CELITE diatomaceous earth and washed copiously with methanol. The volatiles were removed under vacuum and the crude residue was triturated with ether. The solids were collected on a fritted funnel and dried under vacuum. This provided the title compound.

Workup

  1. filtrationthe reaction was filtered through CELITE diatomaceous earth
  2. washwashed copiously with methanol
  3. customThe volatiles were removed under vacuum
  4. customthe crude residue was triturated with ether
  5. customThe solids were collected on a fritted funnel
  6. customdried under vacuum

Sources & evidence

ORD record
ord-d57d16896f9f4187ad5a58a2a543f654
Source dataset
uspto-grants-2006_08
Patent number
US07084156B2

Linked notes

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