Hydroquinone → HCID 19907402, compound

HRID 2371519Notes

Reaction equation

HRID 2371519 reaction equation
[Na].[C:2]1([CH:9]=[CH:8][C:6]([OH:7])=[CH:5][CH:4]=1)[OH:3].Cl.[CH3:11][N:12]([CH3:17])[CH2:13][CH2:14][CH2:15]Cl>CO.Cl>[CH3:11][N:12]([CH3:17])[CH2:13][CH2:14][CH2:15][O:3][C:2]1[CH:9]=[CH:8][C:6]([O:7][CH2:15][CH2:14][CH2:13][N:12]([CH3:17])[CH3:11])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 785HydroquinoneHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 5360545Sodium

Product 1

HCID 19907402HCID 19907402, compoundYield 10.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent3×

Procedure

First, to a solution of 2.3 g of metallic sodium dissolved in 35 ml of absolute methanol, a solution of 2.2 g of hydroquinon in 15 ml of absolute methanol and a solution of 7.9 g of 3-dimethylaminopropyl chloride hydrochloride in 10 ml absolute methanol were added, and the mixture was heated to reflux for 5 hours. After the reaction was completed, the mixture was evaporated under a reduced pressure, and after adding water to the resulting residue, alkalized with 10% sodium hydroxide, salted-out with sodium chloride and extracted with 100 ml of chloroform, the extract was washed with a saturated sodium chloride, and dried over magnesium sulfate. The solvent was removed under a reduced pressure to obtain a reddish liquid, which was dissolved in 1N hydrochloric acid, the solution was washed with chloroform, alkalized with 1N sodium hydroxide and extracted with 100 ml of chloroform. The extract was washed with a saturated sodium chloride aqueous solution and dried over magnesium sulfate, and the solvent was evaporated off under a reduced pressure to obtain 0.60 g of a desired compound as a reddish brown liquid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 5 hours
  3. customthe mixture was evaporated under a reduced pressure
  4. additionafter adding water to the resulting residue
  5. extractionextracted with 100 ml of chloroform
  6. washthe extract was washed with a saturated sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed under a reduced pressure
  9. customto obtain a reddish liquid, which
  10. washthe solution was washed with chloroform
  11. extractionextracted with 100 ml of chloroform
  12. washThe extract was washed with a saturated sodium chloride aqueous solution
  13. dry with materialdried over magnesium sulfate
  14. customthe solvent was evaporated off under a reduced pressure

Sources & evidence

ORD record
ord-4b3f91bd4e524a74bddaf16923c9a3f3
Source dataset
uspto-grants-1992_03
Patent number
US05093370

Reaction notes

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