Thionyl Chloride → Acridine-1-carboxylic acid

HRID 1377423Notes

Reaction equation

HRID 1377423 reaction equation
O.[C:2]1([C:16]([OH:18])=[O:17])[C:15]2[C:6](=[N:7][C:8]3[C:13]([CH:14]=2)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O>O1CCOCC1>[C:2]1([C:16]([OH:18])=[O:17])[C:15]2[C:6](=[N:7][C:8]3[C:13]([CH:14]=2)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86751216HCID 86751216, compound

Product 1

HCID 13777296Acridine-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

Acridine carboxylic acid hydrate (4.6 g, made by Aldrich Chemical Company) was dissolved in 200 ml of dioxane, and 2.4 g of thionyl chloride (made by Kanto Kagaku K.K.) was added thereto dropwise. The reaction was carried out at 60° C. for 1 hour. To this was further added 1.15 g of arylamine and heated at 60° C. for 2 hours. The solution was concentrated under reduced pressure to 50 ml, crystallized by ice cooling, and separated by filtration to obtain 2.2 g of arylamineamide of acridine carboxylic acid.

Workup

  1. concentrationThe solution was concentrated under reduced pressure to 50 ml
  2. customcrystallized by ice cooling
  3. customseparated by filtration

Sources & evidence

ORD record
ord-2e82051f06fb4e7ba99b91d73ad2a959
Source dataset
uspto-grants-1997_09
Patent number
US05665606

Reaction notes

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