Potassium Hydroxide → 104675-34-5

HRID 2309436Notes

Reaction equation

HRID 2309436 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 8028TetrahydrofuranSolvent

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 1.1M 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 supernatant 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 supernatant tetrahydrofuran solution was separated
  6. customevaporated to a solid
  7. customThe solid was recrystallized from 1:4 dichloromethane/EtOAc

Sources & evidence

ORD record
ord-5984602c2ecc493abf0ef515282e4799
Source dataset
uspto-grants-1987_09
Patent number
US04695573

Reaction notes

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