HCID 13935120, compound → 1-Acridinol, 1,2,3,4-tetrahydro-9-((2-(dimethylamino)ethyl)amino)-

HRID 580723Notes

Reaction equation

HRID 580723 reaction equation
[CH3:1][N:2]([CH3:21])[CH2:3][CH2:4][NH:5][C:6]1[C:7]2[C:12]([N:13]=[C:14]3[C:19]=1[C:18](=[O:20])[CH2:17][CH2:16][CH2:15]3)=[CH:11][CH:10]=[CH:9][CH:8]=2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][N:2]([CH3:21])[CH2:3][CH2:4][NH:5][C:6]1[C:7]2[C:12]([N:13]=[C:14]3[C:19]=1[CH:18]([OH:20])[CH2:17][CH2:16][CH2:15]3)=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

4

Reactant 2

HCID 13935120HCID 13935120, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 30256091-Acridinol, 1,2,3,4-tetrahydro-9-((2-(dimethylamino)ethyl)amino)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled solution of 4.4 g of 3,4-dihydro-9-[2-(dimethylamino)ethylamino]acridin-1(2H)-one in 80 ml of tetrahydrofuran was added 8 ml of 1 molar solution of lithium aluminum hydride in THF. This was stirred for 1/2 hour and then quenched with 6 ml of saturated ammonium chloride solution. The inorganics were filtered and rinsed with ethyl acetate. The combined organics were then dried over anhydrous magnesium sulfate and concentrated to give a solid. This was twice recrystallized from acetone/hexane to give 1.4 g of an analytically pure powder, mp 135°-138° C.

Workup

  1. customquenched with 6 ml of saturated ammonium chloride solution
  2. filtrationThe inorganics were filtered
  3. washrinsed with ethyl acetate
  4. dry with materialThe combined organics were then dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto give a solid
  7. customThis was twice recrystallized from acetone/hexane
  8. customto give 1.4 g of an analytically pure powder, mp 135°-138° C.

Sources & evidence

ORD record
ord-41ce5418866f41458d692e526dd039a6
Source dataset
uspto-grants-1988_06
Patent number
US04754050

Reaction notes

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