Sodium Dithionite → HCID 22238098, compound

HRID 1743384Notes

Reaction equation

HRID 1743384 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([CH:9]=[C:10]([N+:12]([O-])=O)[CH3:11])[C:6](OC)=[C:5]([CH3:17])[C:4]=1[CH3:18].[H-].[Al+3].[Li+].[H-].[H-].[H-].[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+]>C1COCC1.C(OCC)(=O)C.C(#N)C.O>[CH3:11][CH:10]1[CH2:9][C:7]2[C:6](=[C:5]([CH3:17])[C:4]([CH3:18])=[C:3]([OH:2])[CH:8]=2)[NH:12]1

Participants

10

Reactant 5

HCID 24489Sodium DithioniteHCID 180504Ceric ammonium nitrateHCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 73877165HCID 73877165, compound

Product 1

HCID 22238098HCID 22238098, compoundYield 45%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent3×HCID 6342AcetonitrileSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 1,4-dimethoxy-2,3-dimethyl-5-(2-nitro-1-propenyl)benzene (2.51 g, 9.99 mmol) in THF (35 mL) was added lithium aluminum hydride (1.0 g, 26 mmol) under ice-cooling, and the mixture was heated to reflux for 6 hours. Hyflo Super-Cel® (5 g) was added to the reaction mixture, and water (1.5 mL) was added dropwise under ice-cooling. The resulting mixture was suspended in ethyl acetate, filtered, concentrated under the reduced pressure to obtain an oil. This was dissolved in acetonitrile (10 mL), a solution of diammonium cerium (IV) nitrate (10.9 g, 19.9 mmol) in acetonitrile (20 mL) and water (20 mL) was added dropwise under ice-cooling, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with water, neutralized with sodium bicarbonate and extracted with ethyl acetate three times. The combined organic layers were washed with water and saturated brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to obtain the solid. This was dissolved in ethyl acetate, mixed with an aqueous solution of sodium hydrosulfite, shaken, and the precipitated solid was filtered to obtain 0.79 g of 2,3-dihydro-2,6,7-trimethyl-1H-indole-5-ol.

Workup

  1. temperaturecooling
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 6 hours
  4. additionwas added dropwise under ice-
  5. temperaturecooling
  6. filtrationfiltered
  7. concentrationconcentrated under the reduced pressure
  8. customto obtain an oil
  9. temperaturecooling
  10. extractionextracted with ethyl acetate three times
  11. washThe combined organic layers were washed with water and saturated brine
  12. dry with materialdried over magnesium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated under reduced pressure
  15. customto obtain the solid
  16. stirringshaken
  17. filtrationthe precipitated solid was filtered

Sources & evidence

ORD record
ord-bec8294d08244548b04dfda5a03c66f0
Source dataset
uspto-grants-2006_03
Patent number
US07008940B1

Reaction notes

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