Potassium Hydroxide → HCID 13935133, compound

HRID 580716Notes

Reaction equation

HRID 580716 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.[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:19][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[C:4]([NH:3][CH2:25][C:24]1[CH:27]=[CH:28][C:21]([F:20])=[CH:22][CH:23]=1)=[C:17]1[C:12]([CH2:13][CH2:14][CH2:15][C:16]1=[O:18])=[N:11]2

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 680214-Fluorobenzyl bromideHCID 1533737HCID 1533737, compound

Product 1

HCID 13935133HCID 13935133, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent2×

Procedure

In 300 ml of toluene and 200 ml of 30% potassium hydroxide were added 9.00 g of 9-amino-6-chloro-3,4-dihydroacridin-1(2H)-one and 3.10 g of tetrabutylammonium hydrogen sulfate catalyst. The mechanically stirred solution was warmed to reflux (90° C.) and 9.54 ml of 4-fluorobenzyl bromide in 50 ml of toluene was added dropwise over 0.5 hours. After refluxing 3 hours the reaction was complete by TLC. It was poured into 500 ml of ice. The aqueous phase was separated and extracted with dichloromethane (DCM hereafter). The organic layers were combined and washed with saturated NaCl solution, dried over anhydrous magnesium sulfate, filtered and evaporated to an oil. The oil was purified by preparative HPLC (1:1 ethyl acetate/hexane) and the product-containing fractions were combined and evaporated to a solid. The solid was recrystallized from 1:1 DCM/pentane to yield 6.10 g of solid, mp 156°-157.5° C.

Workup

  1. temperatureThe mechanically stirred solution was warmed
  2. additionwas added dropwise over 0.5 hours
  3. temperatureAfter refluxing 3 hours the reaction
  4. customThe aqueous phase was separated
  5. extractionextracted with dichloromethane (DCM hereafter)
  6. washwashed with saturated NaCl solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated to an oil
  10. customThe oil was purified by preparative HPLC (1:1 ethyl acetate/hexane)
  11. customevaporated to a solid
  12. customThe solid was recrystallized from 1:1 DCM/pentane

Sources & evidence

ORD record
ord-593e9e4c4d934b37a169a0a567c389cd
Source dataset
uspto-grants-1988_06
Patent number
US04754050

Reaction notes

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