Sodium Iodide → HCID 67363019, compound

HRID 2091468Notes

Reaction equation

HRID 2091468 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:13][CH3:14])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8](Br)=[CH:7]2.[I-:15].[Na+].CNCCNC>O1CCOCC1.[Cu](I)I>[NH2:1][C:2]1[CH:3]=[C:4]([O:13][CH3:14])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([I:15])=[CH:7]2

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 155690063-Bromo-6-methoxyquinolin-8-amine

Product 1

HCID 67363019HCID 67363019, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

In a similar procedure to Step 2 of Example 1 8-amino-3-bromo-6-methoxyquinoline (preparation described in Journal of Pharmaceutical Sciences (1984), 73(12), 1854-6) (6.0 g) is treated with sodium iodide, copper iodide and N,N′-dimethyl-ethane-1,2-diamine in dioxane in a sealed tube under argon, at 120° C. for 14 h. After work-up the crude is purified by flash chromatography (ethyl acetate: cyclohexane, 1:4) to provide 8-amino-3-iodo-6-methoxyquinoline (4.6 g) as a pure product. 1H NMR (CDCl3) δ ppm: 8.70 (1H, d); 8.30 (1H, d); 6.55 (1H, d); 6.35 (1H, d); 5.00 (2H, br s); 3.85 (3H, s). (M+1)+: 301

Workup

  1. customAfter work-up the crude is purified by flash chromatography (ethyl acetate: cyclohexane, 1:4)

Sources & evidence

ORD record
ord-7cd644354e264ca4bacb4255e36fad26
Source dataset
uspto-grants-2013_05
Patent number
US08440595B2

Reaction notes

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