Methylamine → 4-Methylamino-3-nitroquinoline
Reaction equation
[CH3:1][NH2:2].Cl[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6][C:5]=1[N+:14]([O-:16])=[O:15]>O>[CH3:1][NH:2][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6][C:5]=1[N+:14]([O-:16])=[O:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 40% aqueous methylamine was added, in small portions, 30.Og (0.144 mole) of 4-chloro-3-nitroquinoline. The reaction mixture was heated at its reflux temperature for about 0.75 hour. After cooling, the mixture was poured into 300 ml of water. The solid was separated by filtration, and was then suspended in 300 ml of water. Acidification with 6N hydrochloric acid to pH 3 to 4 effected dissolution of most of the solid. Filtration was followed by basification of the filtrate with concentrated ammonium hydroxide to pH 8 to 10 to provide a yellow precipitate. The solid was separated by filtration, washed with water, and recrystallized from ethanol to provide yellow 4-methylamino-3-nitroquinoline, m.p. 168-170° C. Analysis: Calculated for C10H9N3O2 %C, 59.1; %H, 4.5: %N, 20.7: Found: %C, 59.0; %H, 4.2; %N, 20.8.