Acridone → 9-Chloroacridine

HRID 1357480Notes

Reaction equation

HRID 1357480 reaction equation
[CH:1]1[C:14]2[C:13](=O)[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.S(Cl)([Cl:18])=O>CN(C)C=O>[Cl:18][C:13]1[C:14]2[C:5]([N:6]=[C:7]3[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8]3)=[CH:4][CH:3]=[CH:2][CH:1]=2

Participants

4

Reactant 2

HCID 2015AcridoneHCID 24386Thionyl Chloride

Product 1

HCID 710139-ChloroacridineYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

0.488 g (2.5 mmol) of 9-(10H)acridone, 2.5 ml of thionyl chloride and a catalytic amount (a few drops) of dimethylformamide were mixed at 80° C. After 30 min of stirring, the reaction mixture was evaporated, the residue was dissolved in chloroform and poured into cold aqueous ammonia. The ammonia solution was extracted several times with chloroform. The combined organic phases were washed with 2M ammonia solution, dried over sodium sulfate and evaporated to obtain 0.517 g (97%) of 9-chloroacridine.

Workup

  1. customthe reaction mixture was evaporated
  2. dissolutionthe residue was dissolved in chloroform
  3. additionpoured into cold aqueous ammonia
  4. extractionThe ammonia solution was extracted several times with chloroform
  5. washThe combined organic phases were washed with 2M ammonia solution
  6. dry with materialdried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-8481fddf57fc4d3fa3fe5d44fb8c226a
Source dataset
uspto-grants-2003_07
Patent number
US06593324B2

Reaction notes

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