Methyl iodide → HCID 13756050, compound

HRID 2309430Notes

Reaction equation

HRID 2309430 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 150 ml of dichloromethane and 100 ml 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 biphasic mixture was mechanically stirred for 0.5 hour and thereafter 4.4 ml (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 crystalline 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-be2897bd200e464191453a570e6f7dec
Source dataset
uspto-grants-1987_09
Patent number
US04695573

Reaction notes

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