Iodine → 6-Iodo-3,4-dihydroquinolin-2(1H)-one
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]2Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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
- filtrationthe reaction was filtered through CELITE diatomaceous earth
- washwashed copiously with methanol
- customThe volatiles were removed under vacuum
- customthe crude residue was triturated with ether
- customThe solids were collected on a fritted funnel
- customdried under vacuum
Sources & evidence
- ORD record
- ord-d57d16896f9f4187ad5a58a2a543f654
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07084156B2
Reaction notes
Loading…