Potassium Hydroxide → 104675-34-5

HRID 1763009Notes

Reaction equation

HRID 1763009 reaction equation
[CH2:1]([NH:4][C:5]1[C:6]2[C:11]([N:12]=[C:13]3[C:18]=1[CH:17]=[CH:16][CH2:15][CH2:14]3)=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:2][CH3:3].[H-].[H-].[H-].[H-].[Li+].[Al+3].[H-].[NH4+].[Cl-].[OH-:28].[K+]>O1CCCC1.CCOCC>[CH2:1]([NH:4][C:5]1[C:6]2[C:11]([N:12]=[C:13]3[C:18]=1[CH:17]([OH:28])[CH2:16][CH2:15][CH2:14]3)=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:2][CH3:3]

Participants

8

Reactant 5

HCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 166653HydrideHCID 21226445Aluminium lithium hydrideHCID 86743086HCID 86743086, compound

Product 1

HCID 3025633104675-34-5Yield 75%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 50ml of dry tetrahydrofuran was suspended 2.49 g of 3,4-dihydro-9-(n-propylamino)acridin-1(2He-one. The mechanically stirred suspension was cooled in ice and 4.50ml (0.5 eq) of 1.1 M LiAlH4 solution in ether was added dropwise, whereupon a solution formed. After the addition, the reaction appeared complete based on thin layer chromatography analysis. The excess hydride was neutrilized with 0.5ml of saturated NH4Cl solution and therafter 30% potassium hydroxide was added to dissolve the salts. The supernatent tetrahydrofuran solution was separated and evaporated to a solid. The solid was recrystallized from 1:4 dichloromethane/EtOAc to yield 1.88 g (75%) of needles, melting point 164° C.

Workup

  1. temperatureThe mechanically stirred suspension was cooled in ice
  2. customformed
  3. additionAfter the addition
  4. dissolutionto dissolve the salts
  5. customThe supernatent tetrahydrofuran solution was separated
  6. customevaporated to a solid
  7. customThe solid was recrystallized from 1:4 dichloromethane/EtOAc

Sources & evidence

ORD record
ord-05944daccef8466ea604275ec472ce24
Source dataset
uspto-grants-1989_05
Patent number
US04835275

Reaction notes

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