Bromide ion → HCID 13935134, compound

HRID 580717Notes

Reaction equation

HRID 580717 reaction equation
[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[C:14](=[O:16])[CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[OH-].[K+].[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22]Br.[Br-]>CS(C)=O.O>[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][NH:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[C:14](=[O:16])[CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2

Participants

7

Reactant 4

HCID 259Bromide ionHCID 11905alpha-Bromo-o-chlorotolueneHCID 14797Potassium HydroxideHCID 1843619-amino-3,4-dihydroacridin-1(2H)-one

Product 1

HCID 13935134HCID 13935134, compoundYield 53.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a suspension of 9-amino-3,4-dihydroacridin-1(2H)-one (8.0 g) in 75 ml of dimethyl sulfoxide was added pulverized potassium hydroxide (6.2 g). This was stirred for 0.5 hour at ambient temperature. To this solution was added 2-chlorobenzyl bromide (9.4 g). After 1 hour, an additional 1 ml of the bromide was added. This was stirred for an additional hour. At this time, 200 ml of water was added, and the precipitate was filtered and washed with water. The solid was taken up in dichloromethane and dried over anhydrous magnesium sulfate. The compound was purified via flash chromatography to yield 6.75 g of solid, mp 150°-161° C. A portion of this was recrystallized from methanol to give analytically pure needles, mp 162°-165° C. ANALYSIS: Calculated for C20H17ClN2O: 71.32%; 5.09%H; 8.32%N; Found: 71.17%C; 5.25%H; 8.24%N

Workup

  1. additionwas added
  2. waitAfter 1 hour
  3. stirringThis was stirred for an additional hour
  4. filtrationthe precipitate was filtered
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe compound was purified via flash chromatography

Sources & evidence

ORD record
ord-70b10caea4874b44ac8d0f44812c35d9
Source dataset
uspto-grants-1988_06
Patent number
US04754050

Reaction notes

Loading…