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

HRID 2309458Notes

Reaction equation

HRID 2309458 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-e2cb46b16c554c66b331dbc3bfbafc07
Source dataset
uspto-grants-1987_09
Patent number
US04695573

Reaction notes

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