Sodium Hydroxide → HCID 13756051, compound

HRID 1249403Notes

Reaction equation

HRID 1249403 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-eb4a0bbdde7147fdaf286ed3e67c0a32
Source dataset
uspto-grants-1986_12
Patent number
US04631286

Reaction notes

Loading…