Ammonium Chloride → 104628-43-5

HRID 2309482Notes

Reaction equation

HRID 2309482 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][NH:11][C:12]1[C:13]2[C:18]([N:19]=[C:20]3[C:25]=1[C:24](=[O:26])[CH2:23][CH2:22][CH2:21]3)=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl-].[NH4+]>C1COCC1>[O:1]([CH2:8][CH2:9][CH2:10][NH:11][C:12]1[C:13]2[C:18]([N:19]=[C:20]3[C:25]=1[CH:24]([OH:26])[CH2:23][CH2:22][CH2:21]3)=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 13935149HCID 13935149, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 3025629104628-43-5

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 100 ml of dry THF was dissolved 2.47 g of 3,4-dihydro-9-(3-phenoxypropyl)aminoacridin-1(2H)-one. The mechanically stirred solution was cooled in ice under nitrogen and 3.6 ml of 1M LiAlH4 in THF was added dropwise over 5 minutes. After 0.5 hour the reaction was complete by TLC. The reaction was neutralized with 1 ml of saturated ammonium chloride solution and the inorganic salts were filtered off. The filtrate was evaporated to an oil which solidified when triturated with pentane. The solid was recrystallized from 1:1 dichloromethane/pentane to yield after drying 2.17 g of product, mp 138°-140° C.

Workup

  1. temperatureThe mechanically stirred solution was cooled in ice under nitrogen
  2. filtrationthe inorganic salts were filtered off
  3. customThe filtrate was evaporated to an oil which
  4. customtriturated with pentane
  5. customThe solid was recrystallized from 1:1 dichloromethane/pentane
  6. customto yield
  7. dry with materialafter drying 2.17 g of product, mp 138°-140° C.

Sources & evidence

ORD record
ord-76d7e94554a1459998f6a876ce10ce56
Source dataset
uspto-grants-1987_09
Patent number
US04695573

Reaction notes

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