Hydrochloric Acid → Phenyl acridine-9-carboxylate

HRID 850697Notes

Reaction equation

HRID 850697 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:16])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.Cl>S(Cl)(Cl)=O>[CH:11]1[C:12]2[C:7](=[N:6][C:5]3[C:14]([C:13]=2[C:15]([O:17][C:1]2[CH:14]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:16])=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 94721Acridine-9-carboxylic acid

Product 1

HCID 517916Phenyl acridine-9-carboxylate

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

Acridine-9-carboxylic acid (5 g) is suspended in thionyl chloride (75 ml). The mixture is stirred under reflux for four hours. The excess of thionyl chloride is removed by distillation. The residue is suspended in pyridine (75 ml) and the mixture stirred at room temperature for ten minutes. Phenol (4.5 g) is added to the suspension. The resulting reaction mixture is stirred at room temperature for sixteen hours. The resulting solution is poured into one normal hydrochloric acid (200 ml). The precipitate that forms (6.5 g) is isolated by filtration, and recrystallized from benzene/cyclohexane. m.p. 192° C.; IR (KBr): 1750, 1177 cm-1. MS: 299, 206, 178, 152, 151. 1H-NMR: δ7.5-8.5.

Workup

  1. temperatureunder reflux for four hours
  2. customThe excess of thionyl chloride is removed by distillation
  3. stirringthe mixture stirred at room temperature for ten minutes
  4. additionPhenol (4.5 g) is added to the suspension
  5. customThe resulting reaction mixture
  6. stirringis stirred at room temperature for sixteen hours
  7. customis isolated by filtration
  8. customrecrystallized from benzene/cyclohexane

Sources & evidence

ORD record
ord-d4b67d0f369b46dfa699e9a20039c9c4
Source dataset
uspto-grants-2000_01
Patent number
US06018047

Reaction notes

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