Potassium Hydroxide → HCID 13935143, compound

HRID 580720Notes

Reaction equation

HRID 580720 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][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>[F:19][C:20]([F:29])([F:30])[C:21]1[CH:28]=[CH:27][C:24]([CH2:25][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:23][CH:22]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 1843619-amino-3,4-dihydroacridin-1(2H)-one

Product 1

HCID 13935143HCID 13935143, compoundYield 27.7%

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 catalyst. The mechanically stirred mixture was warmed to reflux and 30.0 g of 4-trifluoromethylbenzyl bromide in 50 ml of toluene was added dropwise over 1 hour. After stirring at reflux for 4 hours the reaction was complete by TLC. It was poured into 50 ml of ice and the aqueous layer was separated and extracted with DCM. The organics were combined, washed with saturated NaCl solution, dried over anhydrous magnesium sulfate and evaporated to an oil. The oil was purified by preparative HPLC (ethyl acetate) and the isolated product was recrystallized from dichloromethane/pentane (1:1) to yield 3.87 g of solid, mp 174°-176° C.

Workup

  1. temperatureThe mechanically stirred mixture was warmed
  2. temperatureto reflux
  3. temperatureat reflux for 4 hours the reaction
  4. customthe aqueous layer was separated
  5. extractionextracted with DCM
  6. washwashed with saturated NaCl solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated to an oil
  9. customThe oil was purified by preparative HPLC (ethyl acetate)
  10. customthe isolated product was recrystallized from dichloromethane/pentane (1:1)

Sources & evidence

ORD record
ord-06fc7ab4082e47a89cea0a33a6b198f1
Source dataset
uspto-grants-1988_06
Patent number
US04754050

Reaction notes

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