9-amino-3,4-dihydro-6-fluoroacridin-1(2H)-one → 1-Acridinol, 1,2,3,4-tetrahydro-9-amino-6-fluoro-

HRID 580721Notes

Reaction equation

HRID 580721 reaction equation
[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[C:14](=[O:16])[CH2:13][CH2:12][CH2:11]3)=[CH:7][C:6]([F:17])=[CH:5][CH:4]=2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH:14]([OH:16])[CH2:13][CH2:12][CH2:11]3)=[CH:7][C:6]([F:17])=[CH:5][CH:4]=2

Participants

4

Reactant 2

HCID 139351199-amino-3,4-dihydro-6-fluoroacridin-1(2H)-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 30256071-Acridinol, 1,2,3,4-tetrahydro-9-amino-6-fluoro-Yield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled suspension of 5.0 g of 9-amino-3,4-dihydro-6-fluoroacridin-1(2H)-one in 85 ml of tetrahydrofuran was added 22 ml of 1M solution of lithium aluminum hydride in tetrahydrofuran. This was stirred for 1 hour and then quenched with 8 ml of saturated ammonium chloride solution. The inorganics were filtered and rinsed with ethyl acetate, and the combined organics were dried over anhydrous magnesium sulfate. This was filtered and concentrated to obtain 5.0 g of a powder, mp 203°-206° C. d. This was recrystallized from tetrahydrofuran/hexane to obtain 3.95 g of an analytically pure powder, mp 207°-209° C. d.

Workup

  1. customquenched with 8 ml of saturated ammonium chloride solution
  2. filtrationThe inorganics were filtered
  3. washrinsed with ethyl acetate
  4. dry with materialthe combined organics were dried over anhydrous magnesium sulfate
  5. filtrationThis was filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7a1020d45b674b018def71dd6c9035e9
Source dataset
uspto-grants-1988_06
Patent number
US04754050

Reaction notes

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