Acridine → Acridan

HRID 1907074Notes

Reaction equation

HRID 1907074 reaction equation
[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(=O)(O)[O-].[Na+]>C1COCC1>[CH:1]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 9215AcridineHCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydride

Product 1

HCID 7106AcridanYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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%).

Workup

  1. extractionextracted with methylene chloride
  2. distillationdistilled water
  3. dry with materialThe extracted layer was dried with sodium sulfate so as to filtrate
  4. concentrationconcentrate an organic solvent

Sources & evidence

ORD record
ord-4386054303d14f48a0b1050cf84468e6
Source dataset
uspto-grants-2013_12
Patent number
US08597802B2

Reaction notes

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