Hydrochloric Acid → HCID 10691461, compound

HRID 842685Notes

Reaction equation

HRID 842685 reaction equation
N[C:2]1[C:11]([Cl:12])=[C:10]([Cl:13])[CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([O:16][CH3:17])[C:6]([O:14][CH3:15])=[N:7]2.Cl.N([O-])=O.[Na+].[I-:23].[K+]>CC(C)=O>[Cl:12][C:11]1[C:2]([I:23])=[C:3]2[C:8](=[CH:9][C:10]=1[Cl:13])[N:7]=[C:6]([O:14][CH3:15])[C:5]([O:16][CH3:17])=[N:4]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 106066205-Amino-6,7-dichloro-2,3-dimethoxyquinoxalineHCID 23668193Sodium Nitrite

Product 1

HCID 10691461HCID 10691461, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
10 °C

Procedure

To a mechanically stirred solution of 5-amino-6,7-dichloro-2,3-dimethoxyquinoxaline (Preparation 26, 38.12 g, 0.14 mol) in acetone at 0° C. was added 2M aqueous hydrochloric acid solution (396 mL, 0.79 mol), followed dropwise by addition of 1M aqueous sodium nitrite solution (208 mL, 0.28 mol). After 0.25 hour at 0° C., 5M aqueous potassium iodide solution (278 mL, 1.39 mol) was added maintaining the reaction temperature below 5° C. The mixture was then warmed to 10° C. over 0.5 hour, the acetone removed under reduced pressure and the residue partitioned between water and ethyl acetate. The organic extract was washed with 10% aqueous sodium bisulphite solution, then saturated aqueous sodium bicarbonate solution, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with toluene to give the title compound (16.9 g, 32%).

Workup

  1. temperaturemaintaining the reaction temperature below 5° C
  2. customthe acetone removed under reduced pressure
  3. customthe residue partitioned between water and ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with 10% aqueous sodium bisulphite solution
  6. dry with materialsaturated aqueous sodium bicarbonate solution, dried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography on silica gel
  9. washeluting with toluene

Sources & evidence

ORD record
ord-921ed5c016dc4faea1d9b5086714c576
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

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