Reaction #1994256

ord-4386054303d14f48a0b1050cf84468e6

Reaction equation

[Al+3].[H-].[H-].[H-].[H-].[Li+]
LiAlH4
c1ccc2nc3ccccc3cc2c1
acridine
O=C([O-])O.[Na+]
sodium bicarbonate
→
c1ccc2c(c1)Cc1ccccc1N2
9,10-dihydroacridine
Yield 82.0%

Reactants

[Al+3].[H-].[H-].[H-].[H-].[Li+]
LiAlH4
c1ccc2nc3ccccc3cc2c1
acridine
O=C([O-])O.[Na+]
sodium bicarbonate
—
resultant product

Reagents

None

Solvents

C1CCOC1
THF

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Extractionextracted with methylene chloride
  2. 2
    workup.DISTILLATIONdistilled water
  3. 3
    DryingThe extracted layer was dried with sodium sulfate so as to filtrate
  4. 4
    Concentrationconcentrate an organic solvent

Procedure

Under a nitrogen atmosphere, acridine (17.19 g, 95.92 mmol) and THF (300 ml) were introduced into a round-bottom flask. At 0° C., LiAlH4 (14.56 g, 383.66 mmol) was slowly added in halves twice thereto, followed by stirring at room temperature for 4 hours. At 0° C., the resultant product was slowly added with a sodium bicarbonate solution, and then extracted with methylene chloride and distilled water. The extracted layer was dried with sodium sulfate so as to filtrate and concentrate an organic solvent. Then, the resultant product was columned by methylene chloride and hexane (n-Hexane:MC=8:2) so as to obtain a required compound, 9,10-dihydroacridine (white solid, 14 g, 82%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08597802B2uspto-grants-2013_12