Reaction #465937

ord-e4e9027484294c6a9c469c5a4841e8ab

Reaction equation

O=C1Nc2ccccc2C1=O
isatin
Cl
HCl
→
c1ccc2nc3ccccc3cc2c1
acridine acid

Reactants

O=C1Nc2ccccc2C1=O
isatin
Cl
HCl

Reagents

None

Solvents

[K+].[OH-]
KOH
O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureThe solution was cooled
  2. 2
    Filtrationfiltered after 1 h
  3. 3
    Washwashed with water
  4. 4
    OtherThe solid was air-dried over night
  5. 5
    Washwashed with CH2Cl2
  6. 6
    Otherair-dried

Procedure

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).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06296787B1uspto-grants-2001_10