Benzyl Bromide → 3,4-DIHYDRO-9-[(BENZYL)AMINO]-1(2H)-ACRIDINONE

HRID 1904692Notes

Reaction equation

HRID 1904692 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[C:5]2[C:10]([N:11]=[C:12]3[C:17]=1[C:16](=[O:18])[CH2:15][CH2:14][CH2:13]3)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[CH2:19]([NH:3][C:4]1[C:5]2[C:10]([N:11]=[C:12]3[C:17]=1[C:16](=[O:18])[CH2:15][CH2:14][CH2:13]3)=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 1843619-amino-3,4-dihydroacridin-1(2H)-one

Product 1

HCID 41342583,4-DIHYDRO-9-[(BENZYL)AMINO]-1(2H)-ACRIDINONEYield 41%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

In a biphasic solution consisting of 150 ml of dichloromethane and 100 ml of 50% aqueous NaOH were added 4.00 g of 9-amino-3,4-dihydroacridin-1(2H)-one, and 0.96 g of tetrabutylammonium hydrogensulfate catalyst. The mixture was stirred mechanically for 0.5 hour and thereafter 2.47 ml (1.1 eq) of benzyl bromide was added in one portion. After 4 hours of vigorous stirring, the reaction appeared complete based on thin layer chromatography analysis. The reaction mixture was poured into water/ice and the dichloromethane layer separated, dried over MgSO4 and evaporated to a solid. The solid was recrystallized three times from dichloromethane/hexanes to yield 2.35 g (41%) of product, melting point 162°-163° C.

Workup

  1. waitAfter 4 hours of vigorous stirring
  2. customthe dichloromethane layer separated
  3. dry with materialdried over MgSO4
  4. customevaporated to a solid
  5. customThe solid was recrystallized three times from dichloromethane/hexanes

Sources & evidence

ORD record
ord-7f4d08375a724e0c8cbdbe6e8567eded
Source dataset
uspto-grants-1989_06
Patent number
US04839364

Reaction notes

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