2-Methyl-4-nitroaniline → 2-Chloro-6-methyl-4-nitroaniline
Reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[Cl:12]OC(C)(C)C>C1(C)C=CC=CC=1.O>[Cl:12][C:5]1[CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[CH:8]=[C:2]([CH3:1])[C:3]=1[NH2:4]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
2-methyl-4-nitroaniline (56.0 g, 0.368 mol) was dispersed in toluene (430 ml) in a 1 liter four-neck flask. Tertiary butyl hypochloride (46.0 g, 0.423 mol) was added dropwise thereto, while cooled in iced water and stirred. The mixture was stirred at room temperature for 3 hours. The solids were filtered and washed three times with 200 ml of a 50% aqueous ethanol three times. They were then dried at 40° C. at a reduced pressure to obtain 55.33 g of a yellow solid (production yield 80%). The yellow solid was used in the subsequent step without purification.