Ammonium Chloride → 1-Acridinol, 1,2,3,4-tetrahydro-9-(((3-fluorophenyl)methyl)amino)-

HRID 2309470Notes

Reaction equation

HRID 2309470 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][NH:6][C:7]1[C:8]2[C:13]([N:14]=[C:15]3[C:20]=1[C:19](=[O:21])[CH2:18][CH2:17][CH2:16]3)=[CH:12][CH:11]=[CH:10][CH:9]=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][NH:6][C:7]1[C:8]2[C:13]([N:14]=[C:15]3[C:20]=1[CH:19]([OH:21])[CH2:18][CH2:17][CH2:16]3)=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 13935131HCID 13935131, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 30256191-Acridinol, 1,2,3,4-tetrahydro-9-(((3-fluorophenyl)methyl)amino)-Yield 82.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 100 ml of THF was dissolved 3.00 g of 3,4-dihydro-9-(3-fluorobenzylamino)acridin-1(2H)-one. The mechanically stirred solution was cooled in ice under nitrogen and 4.68 ml of 1M lithium aluminum hydride in THF was added dropwise over 15 minutes. After 0.5 hour, analysis by TLC indicated the reaction was complete, so it was neutralized with 1 ml of saturated ammonium chloride solution and the resulting salts were filtered. The filtrate was evaporated to an oil which crystallized on trituration with pentane. The solid was filtered and recrystallized from 1:1 dichloromethane/pentane to yield 2.50 g of solid, mp 128° C.

Workup

  1. temperatureThe mechanically stirred solution was cooled in ice under nitrogen
  2. filtrationthe resulting salts were filtered
  3. customThe filtrate was evaporated to an oil which
  4. customcrystallized on trituration with pentane
  5. filtrationThe solid was filtered
  6. customrecrystallized from 1:1 dichloromethane/pentane

Sources & evidence

ORD record
ord-98a614144e2d4d06bb615404f1586f9b
Source dataset
uspto-grants-1987_09
Patent number
US04695573

Reaction notes

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