2-(2-Chloro-ethoxy)-6-nitro-phenylamine → 2-(2-Chloro-ethoxy)-4-chloro-6-nitro-phenylamine
Reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:6]=1[NH2:14].[Cl:15]NC(=O)CCC(N)=O>C(#N)C>[Cl:15][C:9]1[CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:6]([NH2:14])=[C:5]([O:4][CH2:3][CH2:2][Cl:1])[CH:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2-(2-chloro-ethoxy)-6-nitro-phenylamine (1a, 30.0 g, 0.14 mol), N-chlorosuccinamide and acetonitrile (1.3 L) was refluxed for 4 hr. The mixture was concentrated under vacuum and the residue was diluted with ethyl acetate (500 mL). The organic layer was washed with water (2×, 250 mL) and brine (250 mL), dried over anhydrous magnesium sulfate, filtered, and the solvent removed under vacuum to give an orange solid residue. Crystallization from ethyl acetate-hexane gave 33.5 g (95.3%) as orange solid, mp 109-110° C.; MS EI m/e 250/252/254 (M+).