Potassium Hydroxide → HCID 13935132, compound

HRID 580715Notes

Reaction equation

HRID 580715 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][CH:8]=[CH:7][CH:6]=2.[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1>C1(C)C=CC=CC=1.C([N+](CCCC)(CCCC)CCCC)CCC>[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH:3][C:4]2[C:5]3[C:10]([N:11]=[C:12]4[C:17]=2[C:16](=[O:18])[CH2:15][CH2:14][CH2:13]4)=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 680214-Fluorobenzyl bromideHCID 1843619-amino-3,4-dihydroacridin-1(2H)-one

Product 1

HCID 13935132HCID 13935132, compound

Reagents, catalysts & solvents 2

HCID 16028TetrabutylammoniumCatalystHCID 1140TolueneSolvent2×

Procedure

In 300 ml of toluene and 200 ml of 30% potassium hydroxide were added 8.00 g of 9-amino-3,4-dihydroacridin-1(2H)-one and 1.92 g of tetrabutylammonium hydrogn sulfate catalyst. The mechanically stirred biphasic solution was heated to reflux and 9.4 ml of 4-fluorobenzyl bromide in 50 ml of toluene was added dropwise. Reflux was continued for a total of 2 hours. The reaction was poured onto ice and the toluene layer was separated. The aqueous phase was extracted with ethyl acetate. The organics were combined, washed with saturated NaCl solution, dried over anhydrous magnesium sulfate, filtered and evaporated to a solid. The solid was recrystallized from 1:1 ethyl acetate/hexane to yield 5.89 g of product, mp 158°-159° C.

Workup

  1. temperatureThe mechanically stirred biphasic solution was heated
  2. temperatureto reflux
  3. temperatureReflux
  4. customwas continued for a total of 2 hours
  5. additionThe reaction was poured onto ice
  6. customthe toluene layer was separated
  7. extractionThe aqueous phase was extracted with ethyl acetate
  8. washwashed with saturated NaCl solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customevaporated to a solid
  12. customThe solid was recrystallized from 1:1 ethyl acetate/hexane

Sources & evidence

ORD record
ord-76c5da72c2334921bfd9a053282970ff
Source dataset
uspto-grants-1988_06
Patent number
US04754050

Reaction notes

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