Ammonium Chloride → 104628-36-6

HRID 1904739Notes

Reaction equation

HRID 1904739 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl-].[NH4+].[F:9][C:10]([F:35])([F:34])[C:11]1[CH:12]=[C:13]([CH:31]=[CH:32][CH:33]=1)[CH2:14][NH:15][C:16]1[C:17]2[C:22]([N:23]=[C:24]3[C:29]=1[C:28](=[O:30])[CH2:27][CH2:26][CH2:25]3)=[CH:21][CH:20]=[CH:19][CH:18]=2>C1COCC1>[F:34][C:10]([F:9])([F:35])[C:11]1[CH:12]=[C:13]([CH:31]=[CH:32][CH:33]=1)[CH2:14][NH:15][C:16]1[C:17]2[C:22]([N:23]=[C:24]3[C:29]=1[CH:28]([OH:30])[CH2:27][CH2:26][CH2:25]3)=[CH:21][CH:20]=[CH:19][CH:18]=2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 13935142HCID 13935142, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 3025626104628-36-6Yield 80.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 100 ml dry THF was dissolved in 3.86 g of 3,4-dihydro-9-(3-trifluoromethylbenzyl)aminoacridin-1(2H)-one. The solution was stirred mechanically under nitrogen and cooled in ice. To it was added 5.2 ml of 1M LiAlH4 in THF dropwise. After stirring an additional 0.5 hour, the reaction was complete. It was neutralized with 1 ml of saturated ammonium chloride and the salts were filtered off. The THF filtrate was evaporated to an oil which solidified upon trituration with pentane. The solid was recrystallized from 1:1 dichloromethane/pentane to yield 3.12 g of solid, mp 154°-155° C.

Workup

  1. temperaturecooled in ice
  2. stirringAfter stirring an additional 0.5 hour
  3. filtrationthe salts were filtered off
  4. customThe THF filtrate was evaporated to an oil which
  5. customThe solid was recrystallized from 1:1 dichloromethane/pentane

Sources & evidence

ORD record
ord-94091cf5c54f4150adee7dfcfaa8304d
Source dataset
uspto-grants-1989_06
Patent number
US04839364

Reaction notes

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