Acridone → 9(10H)-Acridinone, 10-(2-(dimethylamino)ethyl)-

HRID 986252Notes

Reaction equation

HRID 986252 reaction equation
[CH:1]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl.Cl[CH2:20][CH2:21][N:22]([CH3:24])[CH3:23]>CN(C)C=O>[CH3:23][N:22]([CH3:24])[CH2:21][CH2:20][N:6]1[C:5]2[C:14](=[CH:1][CH:2]=[CH:3][CH:4]=2)[C:13](=[O:15])[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]1=2

Participants

5

Reactant 3

HCID 2015AcridoneHCID 24758Sodium hydrideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 30147319(10H)-Acridinone, 10-(2-(dimethylamino)ethyl)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.9 g of acridanone, 1.0 g of sodium hydride and 80 ml of dimethylformamide is stirred for 0.5 hours, then treated with 2.9 g of 1-chloro-2-dimethylaminoethane hydrochloride, stirred at 60° for 18 hours and evaporated. The residue is extracted with methylene chloride. The extract is washed with water, dried over sodium sulfate and evaporated. By crystallization from isopropyl ether there is obtained 10-[2-(dimethylamino)ethyl]-9-acridanone of melting point 145°-146°.

Workup

  1. stirringstirred at 60° for 18 hours
  2. customevaporated
  3. extractionThe residue is extracted with methylene chloride
  4. washThe extract is washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customBy crystallization from isopropyl ether

Sources & evidence

ORD record
ord-e299d4cefb744a1a8a691b151273059b
Source dataset
uspto-grants-1987_12
Patent number
US04711889

Reaction notes

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