Potassium Hydroxide → 2,5-Dimethoxy acridine-9-carboxylic acid

HRID 506432Notes

Reaction equation

HRID 506432 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:19]2[C:14](=[CH:15][C:16]([O:20][CH3:21])=[CH:17][CH:18]=2)[C:12](=O)[C:10]1=[O:11].[OH-:22].[K+]>O>[CH3:21][O:20][C:16]1[CH:17]=[CH:18][C:19]2[C:14](=[C:12]([C:10]([OH:22])=[O:11])[C:5]3[C:4]([N:9]=2)=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][CH:6]=3)[CH:15]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 59017880N-(2-methoxyphenyl)-5-methoxyisatin

Product 1

HCID 590179432,5-Dimethoxy acridine-9-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The crude isatin derivative from step (a) was refluxed in 60 mL of 10% potassium hydroxide in water for 4 hours. The reaction was then cooled to room temperature and filtered. The filtrate was acidified with a mixture of concentrated hydrochloric acid and ice until a dark precipitate separated out. The product was collected by filtration and dried under vacuum. Yield=0.32 g (10%).

Workup

  1. filtrationfiltered
  2. additionThe filtrate was acidified with a mixture of concentrated hydrochloric acid and ice until a dark precipitate
  3. customseparated out
  4. filtrationThe product was collected by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-2f5d74320229466cbc385bdf1138077e
Source dataset
uspto-grants-2010_08
Patent number
US07785904B2

Reaction notes

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