Benzyl Bromide → HCID 13935123, compound

HRID 1904710Notes

Reaction equation

HRID 1904710 reaction equation
[OH-].[K+].[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][C:8]([Cl:19])=[CH:7][CH:6]=2.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:20]([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][C:8]([Cl:19])=[CH:7][CH:6]=2)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 1533737HCID 1533737, compound

Product 1

HCID 13935123HCID 13935123, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent2×

Procedure

In a biphasic solution comprised of 150 ml of toluene and 100 ml of 30% potassium hydroxide were added 3.00 g of 9-amino-6-chloro-3,4-dihydroacridin-1(2H)-one and 0.62 g of tetrabutylammonium hydrogen sulfate. The reaction was mechanically stirred and brought to reflux (b.p. 90° C.) with a steam bath. To the refluxing mixture was added a solution of 3.04 ml of benzyl bromide in 20 ml of toluene over 0.5 hour. Within 1 hour the reaction was complete by TLC. The toluene layer was separated and the aqueous layer was extracted with ethyl acetate. The organics were combined, dried over anhydrous magnesium sulfate, filtered and evaporated to a solid. The solid was recrystallized from dichloromethane/hexane to yield 1.63 g of a solid, mp 141°-143° C.

Workup

  1. temperatureto reflux (b.p. 90° C.) with a steam bath
  2. customThe toluene layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to a solid
  7. customThe solid was recrystallized from dichloromethane/hexane

Sources & evidence

ORD record
ord-fa002ec82f21463184509763ec48a594
Source dataset
uspto-grants-1989_06
Patent number
US04839364

Reaction notes

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