Ammonium Chloride → Suronacrine

HRID 2309437Notes

Reaction equation

HRID 2309437 reaction equation
[CH2:1]([NH:8][C:9]1[C:10]2[C:15]([N:16]=[C:17]3[C:22]=1[C:21](=[O:23])[CH2:20][CH2:19][CH2:18]3)=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[H-].[NH4+].[Cl-]>O1CCCC1.CCOCC>[CH2:1]([NH:8][C:9]1[C:10]2[C:15]([N:16]=[C:17]3[C:22]=1[CH:21]([OH:23])[CH2:20][CH2:19][CH2:18]3)=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 166653HydrideHCID 41342583,4-DIHYDRO-9-[(BENZYL)AMINO]-1(2H)-ACRIDINONEHCID 21226445Aluminium lithium hydride

Product 1

HCID 60601SuronacrineYield 75.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 75 ml of dry tetrahydrofuran was dissolved 3.81 g of 9-benzylamino-3,4-dihydroacridin-1(2H)-one with mechanical stirring. The solution was cooled in ice under N2 and 5.9 ml (0.5 eq) of 1.1M LiAlH4 solution in ether was added dropwise. After 0.5 hour the reaction was complete based on thin layer chromatography analysis. The excess hydride was neutralized with 0.5 ml of saturated NH4Cl solution and the inorganic salts were extracted into 30% potassium hydroxide. The tetrahydrofuran solution was decanted and evaporated to a solid which was recrystallized from 1:10 dichloromethane/EtOAc to yield 2.89 g (75%) of a solid, melting point 159° C.

Workup

  1. temperatureThe solution was cooled in ice under N2
  2. extractionthe inorganic salts were extracted into 30% potassium hydroxide
  3. customThe tetrahydrofuran solution was decanted
  4. customevaporated to a solid which
  5. customwas recrystallized from 1:10 dichloromethane/EtOAc

Sources & evidence

ORD record
ord-97a0d08b470a44e183607486e111cb4b
Source dataset
uspto-grants-1987_09
Patent number
US04695573

Reaction notes

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