Hydrochloric Acid → Acridine

HRID 369524

Reaction equation

HRID 369524 reaction equation
Cl[C:2]1[CH:3]=[C:4](C(O)=O)[C:5]2[C:14]([CH:15]=1)=[N:13][C:12]1[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[CH:6]=2.N1C2C(=CC=CC=2)C(=O)C1=O.Cl>[OH-].[K+].O>[CH:3]1[CH:4]=[C:5]2[CH:6]=[C:7]3[C:12](=[N:13][C:14]2=[CH:15][CH:2]=1)[CH:11]=[CH:10][CH:9]=[CH:8]3

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7054IsatinHCID 180067903-Chloroacridinecarboxylic acid

Product 1

HCID 9215Acridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

3-Chloroacridinecarboxylic acid. The isatin product from step (a) was refluxed in 300 mL of 10% KOH solution in water for ca. 48 h. The solution was cooled and acidified to pH 2-3 with HCl. The yellow solid was suction filtered after 1 h and then washed with water. The solid was air-dried over night, washed with CH2Cl2 and then air-dried yielding 23.76 g of the acridine acid. 1H NMR (DMSO-d6) δ 7.72-8.30 (m, 7H).

Workup

  1. temperatureThe solution was cooled
  2. filtrationfiltered after 1 h
  3. washwashed with water
  4. customThe solid was air-dried over night
  5. washwashed with CH2Cl2
  6. customair-dried

Sources & evidence

ORD record
ord-697c4646b6fa4d65b7c64c5dda08e5c1
Source dataset
uspto-grants-2000_10
Patent number
US06139782

Linked notes

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