Thionyl Chloride → 9-Acridinecarbonyl chloride

HRID 1375315Notes

Reaction equation

HRID 1375315 reaction equation
[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[C:15]([OH:17])=O)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:20])=O>>[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[C:15]([Cl:20])=[O:17])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 94721Acridine-9-carboxylic acid

Product 1

HCID 6099609-Acridinecarbonyl chlorideYield 94%

Procedure

Acridine-9-carboxylic acid (1.730 g, 10 mmol) was dissolved in thionyl chloride (25 ml) and the solution was refluxed for 6 hours. The solution was concentrated in vacuo and hexane was added slowly to precipitate the product. The mixture was filtered to give a yellow solid (1.721 g, 94%), mp 218–9° C.

Workup

  1. temperaturethe solution was refluxed for 6 hours
  2. concentrationThe solution was concentrated in vacuo and hexane
  3. additionwas added slowly
  4. customto precipitate the product
  5. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-2624fa4795cf44d5bce7d277faa270a8
Source dataset
uspto-grants-2007_01
Patent number
US07169554B2

Reaction notes

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