Reaction #607453

Reaction equation

ammonia

3-nitro-4-chloroquinoline

→

Compound 7

3-nitro-4-aminoquinoline

Solvents

toluene

propanol

Conditions

Workup

1. 1
   Otherwas formed
2. 2
   OtherDuring the course of the reaction
3. 3
   TemperatureAfter cooling
4. 4
   Otherthe solid was separated by filtration
5. 5
   Washwashed successfully with toluene/2-propanol (70:30), ether and cold water until Cl−
6. 6
   FiltrationThe solid was filtered off
7. 7
   Otherdried at 80° C

Procedure

Compound 7 was prepared as described elsewhere [Van Galen, P. J. M. et. al. (1991) ibid.]. In brief, ammonia gas was passed, while stirring, through a solution of 3-nitro-4-chloroquinoline 6 (7.0 g, 30 mmol) in toluene (95 ml) and propanol (15 ml) till the product was formed. During the course of the reaction, the temperature was gradually raised till 70° C. After cooling, the solid was separated by filtration and washed successfully with toluene/2-propanol (70:30), ether and cold water until Cl− could no longer be detected. The solid was filtered off and dried at 80° C. Yield: 6.1 g (95%). Mp.: 255-257° C. 1H NMR (DMSO-d6): δ 7.50-7.66 (m, 1H, Ar); 7.81-7.92 (m, 2H, Ar); 8.59 (d, 1H, J=8.0 Hz, Ar); 9.03 (broad s, 2H, NH2); 9.18 (s, 1H, Ar)

Source