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

HRID 1763041Notes

Reaction equation

HRID 1763041 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.[Al].[Li].[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 16211445Aluminum;lithium

Product 1

HCID 30256191-Acridinol, 1,2,3,4-tetrahydro-9-(((3-fluorophenyl)methyl)amino)-Yield 0.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 100 ml of THF was dissolved 300 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 hidride in THF was added dropwise over 15 minutes. After 0.5 hours, 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 evaported 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. customcrystallized on trituration with pentane
  4. filtrationThe solid was filtered
  5. customrecrystallized from 1:1 dichloromethane/pentane

Sources & evidence

ORD record
ord-1c778142f18943028aba466618f328bd
Source dataset
uspto-grants-1989_05
Patent number
US04835275

Reaction notes

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