Sodium Hydroxide → HCID 13756051, compound

HRID 580696Notes

Reaction equation

HRID 580696 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.[CH2:19](I)[CH2:20][CH3:21]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[CH2:19]([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)[CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 336431-IodopropaneHCID 1843619-amino-3,4-dihydroacridin-1(2H)-one

Product 1

HCID 13756051HCID 13756051, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

In a mixture consisting of 150 ml of dichloromethane and 100 ml of 50% NaOH were combined 5.00 g of 9-amino-3,4-dihydroacridin-1(2H)-one and 0.80 g (0.10 eq) of tetrabutylammonium hydrogensulfate. The biphasic mixture was stirred for 0.5 hour and thereafter 6.9 ml (3 eq) of n-propyl iodide was added and the stirring at room temperature was continued for 2 days during which three more portions of the above quantities of the alkylating agent were added at 12 hour intervals. The reaction was then complete based on thin layer chromatography analysis. The organics were separated and purified by passing through an alumina column (dichloromethane). The product was recrystallized from dichloromethane/Et2O to yield 3.77 g (63%) of a solid, melting point 145° C.

Workup

  1. waitthe stirring at room temperature was continued for 2 days during which three more portions of the above quantities of the alkylating agent
  2. additionwere added at 12 hour intervals
  3. customThe organics were separated
  4. custompurified
  5. customThe product was recrystallized from dichloromethane/Et2O

Sources & evidence

ORD record
ord-392a3b973d034727a204823490396eb1
Source dataset
uspto-grants-1988_06
Patent number
US04754050

Reaction notes

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