Potassium Hydroxide → 2-Methoxyacridine-9-carboxylic acid

HRID 11200Notes

Reaction equation

HRID 11200 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:12](=O)[C:10]2=[O:11])=[CH:5][CH:4]=1.[OH-:20].[K+]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[C:5](=[C:12]([C:10]([OH:20])=[O:11])[C:14]3[C:19]([N:9]=2)=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:4]=1

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 139250941-(4-Methoxyphenyl)indoline-2,3-dione

Product 1

HCID 219722722-Methoxyacridine-9-carboxylic acid

Procedure

The crude N-(4-methoxyphenyl)isatin from the above was suspended in 10% aqueous potassium hydroxide (150 ml) and refluxed under a nitrogen atmosphere. After 4 hours, the reflux was stopped and the reaction was filtered while still hot. The filtrate was diluted with water (˜150 ml) and ice. This solution was then acidified with concentrated hydrochloric acid. A yellow precipitate appeared which was collected by filtration. The precipitate was rinsed with cold water and ether and then air-dried. The dried residue was then transferred to a round-bottom flask with the aid of methanol and the partial solution was evaporated to dryness. The resulting residue was evaporated to dryness from toluene twice. A yellowish-brown powder was recovered in 1.15 g. TLC (1:4, methanol:chloroform) indicated a clean reaction; Rf (product)=0.14. This material was used as such for the next reaction.

Workup

  1. temperaturerefluxed under a nitrogen atmosphere
  2. filtrationthe reaction was filtered while still hot
  3. additionThe filtrate was diluted with water (˜150 ml) and ice
  4. filtrationwas collected by filtration
  5. washThe precipitate was rinsed with cold water and ether
  6. customair-dried
  7. customThe dried residue was then transferred to a round-bottom flask with the aid of methanol
  8. customthe partial solution was evaporated to dryness
  9. customThe resulting residue was evaporated to dryness from toluene twice
  10. customA yellowish-brown powder was recovered in 1.15 g
  11. customa clean reaction
  12. customsuch for the next reaction

Sources & evidence

ORD record
ord-4f33cc32c4cf4ebcbe5ac5bfe604c53b
Source dataset
uspto-grants-2006_08
Patent number
US07097995B2

Reaction notes

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