3,4-dihydro-6-fluoro-9-(2-trifluoromethylbenzylamino)acridin-1(2H)-one → 1-Acridinol, 1,2,3,4-tetrahydro-6-fluoro-9-(((2-(trifluoromethyl)phenyl)methyl)amino)-

HRID 2309477Notes

Reaction equation

HRID 2309477 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]([NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]([F:27])([F:26])[F:25])=[C:11]1[C:6]([CH2:7][CH2:8][CH2:9][C:10]1=[O:28])=[N:5]2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]([NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]([F:25])([F:27])[F:26])=[C:11]1[C:6]([CH2:7][CH2:8][CH2:9][CH:10]1[OH:28])=[N:5]2

Participants

4

Reactant 2

HCID 139351393,4-dihydro-6-fluoro-9-(2-trifluoromethylbenzylamino)acridin-1(2H)-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 30256251-Acridinol, 1,2,3,4-tetrahydro-6-fluoro-9-(((2-(trifluoromethyl)phenyl)methyl)amino)-Yield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled solution of 5.7 g of 3,4-dihydro-6-fluoro-9-(2-trifluoromethylbenzylamino)acridin-1(2H)-one in 80 ml of tetrahydrofuran was added 7.5 ml of 1 molar solution of lithium aluminium hydride in THF. This was stirred for 0.5 hour and then quenched with 6 ml of saturated ammonium chloride solution. The inorganics were filtered, rinsed with ethyl acetate and the combined organics were dried over anhydrous magnesium sulfate. This was concentrated to a solid which was triturated with ether to give 5.1 g of a powder. This was twice recrystallized from ethyl acetate/hexane to give 3.1 g of analytically pure crystals, mp 149°-153° 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 dried over anhydrous magnesium sulfate
  5. concentrationThis was concentrated to a solid which
  6. customwas triturated with ether

Sources & evidence

ORD record
ord-ac4f1f68bd7045eaa65383ccba63cd0f
Source dataset
uspto-grants-1987_09
Patent number
US04695573

Reaction notes

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