Iodine → 6-chloro-3-iodo-7-methoxy-2-methylquinolin-4(1H)-one

HRID 1908991Notes

Reaction equation

HRID 1908991 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][C:7]([CH3:14])=[CH:6][C:5]2=[O:15].C(N)CCC.[I:21]I.[I-].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][C:7]([CH3:14])=[C:6]([I:21])[C:5]2=[O:15]

Participants

6

Reactant 4

HCID 807IodineHCID 4875Potassium IodideHCID 8007ButylamineHCID 497814646-chloro-7-methoxy-2-methylquinolin-4(1H)-one

Product 1

HCID 670167026-chloro-3-iodo-7-methoxy-2-methylquinolin-4(1H)-oneYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-chloro-7-methoxy-2-methylquinolin-4(1H)-one (6.43 g, 28.7 mmol) and n-butylamine (28 ml, 287 mmol) in dimethylformamide (57 ml) cooled by a room temperature water bath was added iodine (7.30 g, 28.7 mmol) in a saturated solution of aqueous potassium iodide (29 ml). The reaction mixture was stirred 12 hours at room temperature. Residual iodine was quenched with 0.1 M aqueous sodium thiosulfate, and the resulting solution was concentrated in vacuo. The residue was resuspended in water and filtered to give 8.93 g (89% yield) of 6-chloro-3-iodo-7-methoxy-2-methylquinolin-4(1H)-one as a light brown powder.

Workup

  1. customResidual iodine was quenched with 0.1 M aqueous sodium thiosulfate
  2. concentrationthe resulting solution was concentrated in vacuo
  3. filtrationfiltered

Sources & evidence

ORD record
ord-02c63bc650d64ef1a6497d9fb85a30e3
Source dataset
uspto-grants-2013_12
Patent number
US08598354B2

Reaction notes

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