Potassium Hydroxide → 104675-34-5

HRID 1249406Notes

Reaction equation

HRID 1249406 reaction equation
[CH2:1]([NH:4][C:5]1[C:6]2[C:11]([N:12]=[C:13]3[C:18]=1[C:17](=[O:19])[CH2:16][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-].[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:19])[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 13756051HCID 13756051, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 3025633104675-34-5Yield 75%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In 50 ml of dry tetrahydrofuran was suspended 2.49 g of 3,4-dihydro-9-(n-propylamino)acridin-1(2H)-one. The mechanically stirred suspension was cooled in ice and 4.50 ml (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 neutralized with 0.5 ml of saturated NH4Cl solution and thereafter 30% potassium hydroxide was added to dissolve the salts. The supernatent tetrahydrofuran solution was separted 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. customevaporated to a solid
  6. customThe solid was recrystallized from 1:4 dichloromethane/EtOAc

Sources & evidence

ORD record
ord-5d1bdaf362544ed59b671361cd91602b
Source dataset
uspto-grants-1986_12
Patent number
US04631286

Reaction notes

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