Methyl iodide → HCID 13756050, compound

HRID 1763004Notes

Reaction equation

HRID 1763004 reaction equation
[OH-].[Na+].[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.[CH3:19]I>ClCCl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:19][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 6328Methyl iodideHCID 14798Sodium HydroxideHCID 1843619-amino-3,4-dihydroacridin-1(2H)-one

Product 1

HCID 13756050HCID 13756050, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

In 150ml of dichloromethane and 100ml of 50% NaOH were added 5.00 g of 9-amino-3,4-dihydroacridin-1(2H)-one and 0.80 g (0.1 eq) of tetrabutylammonium hydrogensulfate. The bipasic mixture was mechanically stirred for 0.5 hour and thereafter 4.4ml (3 eq) of CH3I was added. The reaction mixture was stirred overnight. Analysis of the reaction mixture indicated that the starting material was completely consumed. The reaction mixture was poured into cold water and the dichloromethane layer was evaporated, dried over MgSO4 and filtered through alumina and the solvent was evaporated to afford a solid. The solid was recrystallized from dichloromethane/hexanes to yield 3.73 g (70%) of crystallized product after drying, melting point 116°-117° C.

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. customwas completely consumed
  3. additionThe reaction mixture was poured into cold water
  4. customthe dichloromethane layer was evaporated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered through alumina
  7. customthe solvent was evaporated
  8. customto afford a solid
  9. customThe solid was recrystallized from dichloromethane/hexanes

Sources & evidence

ORD record
ord-68982a7e238444fd80cf3adccae31aa0
Source dataset
uspto-grants-1989_05
Patent number
US04835275

Reaction notes

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