Sodium Dithionite → HCID 22238082, compound

HRID 1743388Notes

Reaction equation

HRID 1743388 reaction equation
Cl.CO[C:4]1[C:9]([CH3:10])=[C:8]([CH3:11])[C:7]([O:12]C)=[CH:6][C:5]=1[CH2:14][CH2:15][NH2:16].[N+]([O-])([O-])=O.[Ce+4].[NH4+].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.C(=O)(O)[O-].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O.C(#N)C.C(OCC)(=O)C>[CH3:11][C:8]1[C:9]([CH3:10])=[C:4]2[C:5]([CH2:14][CH2:15][NH:16]2)=[CH:6][C:7]=1[OH:12]

Participants

8

Reactant 4

HCID 24489Sodium DithioniteHCID 180504Ceric ammonium nitrateHCID 516892Sodium BicarbonateHCID 222380902C-G (hydrochloride)

Product 1

HCID 22238082HCID 22238082, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent4×HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 2,5-dimethoxy-3,4-dimethylbenzeneethaneamine hydrochloride (12.3 g, 0.05 mol) in water (50 mL) was added dropwise a solution of diammonium cerium (IV) nitrate (60.3 g, 0.11 mol) in acetonitrile (100 mL) and water (100 mL) under ice-cooling over 30 minutes, and the mixture was stirred at room temperature for 1 hour. The reaction solution was added dropwise to a suspension of a sodium bicarbonate (65.6 g, 0.78 mol) in water (250 mL)-ethyl acetate (250 mL), and the mixture was stirred at room temperature for 10 minutes. This mixture was filtered, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate two times. The combined organic layers were washed with water, mixed with a 80% sodium hydrosulfite (21.8 g, 0.10 mol) solution in water (200 mL), shaken, and the aqueous layer was separated. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was recrystallized from ethanol-diisopropyl ether to obtain 5.79 g of the title compound.

Workup

  1. temperaturecooling over 30 minutes
  2. stirringthe mixture was stirred at room temperature for 10 minutes
  3. filtrationThis mixture was filtered
  4. customthe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate two times
  6. washThe combined organic layers were washed with water
  7. stirringshaken
  8. customthe aqueous layer was separated
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was recrystallized from ethanol-diisopropyl ether

Sources & evidence

ORD record
ord-6bd88cef4b8547ee88aea61f64ac367e
Source dataset
uspto-grants-2006_03
Patent number
US07008940B1

Reaction notes

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