Reaction #1379890

Reaction equation

sodium hydroxide

5-aminoquinoline

crotonic acid

water

→

cream solid

Yield 51.0%

3-(quinolin-5-ylamino)-butyric Acid

Yield 51.0%

Solvents

toluene

Conditions

Workup

1. 1
   Temperatureat reflux for 48 h
2. 2
   Temperatureto cool to ambient,
3. 3
   Extractionthe filtrate extracted with diethyl ether (3×100 ml)
4. 4
   OtherThe precipitate which formed
5. 5
   Filtrationwas collected by filtration
6. 6
   Washwashed first with water (200 ml)
7. 7
   Dryingwith acetone (200 ml) before being dried

Procedure

A mixture of 5-aminoquinoline (9.9 g, 0.069 mol) and crotonic acid (8.9 g, 0.103 mol) in toluene (35 ml) was stirred at reflux for 48 h. The reaction mixture was allowed to cool to ambient, added to water (500 ml) and the pH adjusted to 9 to 10 by the addition of 2N sodium hydroxide. The reaction mixture was screened and the filtrate extracted with diethyl ether (3×100 ml). The pH of the aqueous layer was first adjusted to pH2 with concentrated HCl and then to pH7 with calcium hydroxide. The precipitate which formed was collected by filtration, washed first with water (200 ml) and then with acetone (200 ml) before being dried to give 8.1 g of a cream solid.

Source