Water → HCID 60046937, compound

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>C(O)(=O)C>[Cl:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][C:3]([N+:13]([O-:15])=[O:14])=[C:2]2[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Procedure

0.6 g (2.46 mmol) 4,6-dichloro-3-nitro-quinoline (Example 23c) and 0.247 ml (2.71 mmol) aniline in 4 ml acetic acid are stirred at rt for 4 h (tlc-control). A precipitate is formed. The reaction mixture is poured into 150 ml water. The solid is filtered off and washed with water and hexane. The filtrate is dissolved in ca. 50 ml diethylether, filtered from insoluble material, and the solvent is evaporated. The residue, yellow crystals, is dried at 60° C. over night. mp: 174-175° C. MS: 300 (M++1); HPLC: tret=10.53 min (Grad 1).