Sodium Hydroxide → HCID 13756051, compound

HRID 2309432Notes

Reaction equation

HRID 2309432 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-0cd46a47dc9142ac9a7b56bf8211a93d
Source dataset
uspto-grants-1987_09
Patent number
US04695573

Reaction notes

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