Reaction #2460283

Reaction equation

N-(4-methoxyphenyl)isatin

potassium hydroxide

→

2-Methoxy-acridine-9-carboxylic acid

Conditions

Workup

1. 1
   Temperaturerefluxed under a nitrogen atmosphere
2. 2
   Filtrationthe reaction was filtered while still hot
3. 3
   workup.ADDITIONThe filtrate was diluted with water (˜150 ml) and ice
4. 4
   Filtrationwas collected by filtration
5. 5
   WashThe precipitate was rinsed with cold water and ether
6. 6
   Otherair-dried
7. 7
   OtherThe dried residue was then transferred to a round-bottom flask with the aid of methanol
8. 8
   Otherthe partial solution was evaporated to dryness
9. 9
   OtherThe resulting residue was evaporated to dryness from toluene twice
10. 10
    OtherA yellowish-brown powder was recovered in 1.15 g
11. 11
    Othera clean reaction
12. 12
    Othersuch for the next reaction

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.

Source