Potassium Hydroxide → HCID 13935138, compound

HRID 580718Notes

Reaction equation

HRID 580718 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]([F:30])([F:29])[C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23]Br>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[F:19][C:20]([F:29])([F:30])[C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23][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

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzeneHCID 1843619-amino-3,4-dihydroacridin-1(2H)-one

Product 1

HCID 13935138HCID 13935138, compoundYield 46.5%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent2×

Procedure

In 300 ml of toluene and 200 ml of 30% potassium hydroxide were combined 8.00 g of 9-amino-3,4-dihydroacridin-1(2H)-one and 3.20 g of tetrabutylammonium hydrogen sulfate. The biphasic mixture was mechanically stirred and warmed to reflux (90° C.) and 30.0 g of 2-trifluoromethylbenzyl bromide in 50 ml of toluene was added dropwise over 1 hour. After the addition, heating was maintained for 2 hours during which the reaction went to completion. It was poured into 500 ml of ice and the layers were separated. The aqueous phase was extracted with DCM. The organic solutions were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and evaporated to an oil which was purified by preparative HPLC (ethyl acetate). The product-containing fractions were evaporated to a solid which was recrystallized from 1:1 ethyl acetate/hexanes to yield 6.49 g of solid, mp 167° C.

Workup

  1. temperaturewarmed
  2. additionwas added dropwise over 1 hour
  3. additionAfter the addition
  4. temperatureheating
  5. temperaturewas maintained for 2 hours during which the reaction
  6. customthe layers were separated
  7. extractionThe aqueous phase was extracted with DCM
  8. washwashed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customevaporated to an oil which
  12. customwas purified by preparative HPLC (ethyl acetate)
  13. customThe product-containing fractions were evaporated to a solid which
  14. customwas recrystallized from 1:1 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-c4a2a573576b4a418fed6e043e9e6e47
Source dataset
uspto-grants-1988_06
Patent number
US04754050

Reaction notes

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