HCID 10979581, compound → HCID 10378569, compound

HRID 1060619Notes

Reaction equation

HRID 1060619 reaction equation
[Br:1][C:2]1[C:3]([O:15]C)=[C:4]2[C:9](=[C:10]([O:12]C)[CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[Cl:14].[N+]([O-])([O-])=O.[NH4+].[Ce]>C(#N)C.O>[Br:1][C:2]1[C:3](=[O:15])[C:4]2[C:5]([Cl:14])=[CH:6][CH:7]=[N:8][C:9]=2[C:10](=[O:12])[CH:11]=1

Participants

5

Reactant 2

HCID 10979581HCID 10979581, compound2×HCID 57418452Ammonium cerium-nitrate

Product 1

HCID 10378569HCID 10378569, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a cooled (0° C.) solution of 6-bromo-4-chloro-5,8-dimethoxyquinoline (compound 9) (215 mg, 0.71 mmol) in acetonitrile (10 ml) was added a cooled solution of cerium ammonium nitrate (2 g, 3.67 mmol) in water (10 ml), with stirring. The solution was stirred at room temperature for 90 min, diluted with water (20 ml) and extracted with chloroform (3×60 ml). The chloroform layers were joined, dried over sodium sulphate and evaporated, yielding 153 mg (79%) of compound 10.

Workup

  1. stirringThe solution was stirred at room temperature for 90 min
  2. extractionextracted with chloroform (3×60 ml)
  3. dry with materialdried over sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-02da4eb9a61149af85609ed80f22ffb9
Source dataset
uspto-grants-2003_02
Patent number
US06525063B2

Reaction notes

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