o-Xylyl bromide → HCID 14253836, compound

HRID 2309449Notes

Reaction equation

HRID 2309449 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+].[CH3:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22]Br.C(Br)C1C=CC=CC=1>CS(C)=O.CCOCC.O>[CH3:19][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

8

Reactant 4

HCID 6992o-Xylyl bromideHCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 1843619-amino-3,4-dihydroacridin-1(2H)-one

Product 1

HCID 14253836HCID 14253836, compoundYield 63.4%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

9-amino-3,4-dihydroacridin-1(2H)-one (7.63 g) was suspended in 75 ml of dimethylsulfoxide and 5 g of pulverized 85% potassium hydroxide was added. After 45 minutes a homogeneous solution was obtained to which was added 7.0 g of 2-methylbenzyl bromide. The reaction mixture was stirred for 30 minutes and then additional 2.0 g of the benzyl bromide was added. After 60 more minutes 300 ml of water and 30 ml of ether were added to the reaction. The precipitated product was filtered off and washed with additional ether, then flushed over a short magnesium silicate column with ethyl acetate. After evaporating the solvent, the product was again washed with cold ether to give 7.21 g of product.

Workup

  1. customAfter 45 minutes a homogeneous solution was obtained to which
  2. filtrationThe precipitated product was filtered off
  3. washwashed with additional ether
  4. customflushed over a short magnesium silicate column with ethyl acetate
  5. customAfter evaporating the solvent
  6. washthe product was again washed with cold ether

Sources & evidence

ORD record
ord-dba0e8fa40254cb796446c3e81a97b6a
Source dataset
uspto-grants-1987_09
Patent number
US04695573

Reaction notes

Loading…