HCID 15571672, compound → 3-methoxyacridine

HRID 2188230Notes

Reaction equation

HRID 2188230 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:15]([CH:16]=1)=[N:14][C:13]1[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=1)[C:7]=2Cl>Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:15]([CH:16]=1)=[N:14][C:13]1[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH:7]=2

Participants

3

Reactant 1

HCID 15571672HCID 15571672, compound

Product 1

HCID 98371983-methoxyacridineYield 19.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 93.34 g of 3-methoxy-9-chloroacridine (0.38 mol) in 2 L of 5 N HCl was stirred at reflux for 40 h. The reaction mixture was cooled to room temperature and the precipitate was collected by suction filtration, washed with 1 L of water, and dried. The solid was stirred in 1 L of methanol and the insoluble precipitate was collected by filtration to afford 15.3 g of the desired 3-methoxy-acridine. The filtrate was concentrated in vacuo and chromatographed on silica gel in 20% methanol in CH2Cl2 to afford a dark brown solid. The solid was triturated in 200 mL of methanol and the insoluble precipitate was collected by filtration to afford a second crop of product. The filtrate was concentrated to a thick solution, and a third crop of product was collected by filtration. The second and third crop of product were combined to give 2.6 g of 3-methoxyacridone, for a combined total of 17.9 g (21%).

Workup

  1. temperatureat reflux for 40 h
  2. filtrationthe precipitate was collected by suction filtration
  3. washwashed with 1 L of water
  4. customdried
  5. filtrationthe insoluble precipitate was collected by filtration

Sources & evidence

ORD record
ord-c3d238340d114dfbb3b0d428e3bd1f19
Source dataset
uspto-grants-2002_06
Patent number
US06410732B2

Reaction notes

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