Sodium Dithionite → HCID 22506872, compound

HRID 985587Notes

Reaction equation

HRID 985587 reaction equation
CO[C:3]1[C:8]([CH3:9])=[CH:7][C:6]([O:10]C)=[C:5]([CH3:12])[C:4]=1[CH2:13][CH:14]([NH2:16])[CH3:15].[N+]([O-])([O-])=O.[NH4+].[NH4+].[Ce+4].[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+]>C(#N)C.O.C(OCC)(=O)C>[OH:10][C:6]1[C:5]([CH3:12])=[C:4]2[C:3](=[C:8]([CH3:9])[CH:7]=1)[NH:16][CH:14]([CH3:15])[CH2:13]2

Participants

8

Reactant 4

HCID 24489Sodium DithioniteHCID 180504Ceric ammonium nitrateHCID 516892Sodium BicarbonateHCID 22506827HCID 22506827, compound

Product 1

HCID 22506872HCID 22506872, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To the solution of 1-(2,5-dimethoxy-3,6-dimethylphenyl)-2-propanamine (2.2 g, 9.4 mmol) in acetonitrile (10 ml) was added dropwise a solution of cerium (IV) diammonium nitrate (10.0 g, 18.2 mmol) in acetonitrile (20 ml) and water (20 ml) with cooling on ice, and stirred at room temperature for 2 hours. The reaction mixture was diluted with water, neutralized with sodium hydrogen carbonate, and extracted three times with ethyl acetate. The organic layers were combined, washed with water and saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to obtain a solid. The solid was dissolved in ethyl acetate, combined with an aqueous solution of sodium hydrosulfite and shaken to precipitate a solid, which was collected by filtration to obtain 1.2 g of the title compound.

Workup

  1. temperaturewith cooling on ice
  2. extractionextracted three times with ethyl acetate
  3. washwashed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto obtain a solid
  8. stirringshaken
  9. customto precipitate a solid, which
  10. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-07bcb0cc90f747a79ecd2f467bbd828c
Source dataset
uspto-grants-2005_03
Patent number
US06872718B1

Reaction notes

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