4-Aminophenol → 2-Chloro-3-(4-hydroxyanilino)-1,4-naphthoquinone
Reaction equation
Cl[C:2]1[C:3](=[O:14])[C:4]2[C:9]([C:10](=[O:13])[C:11]=1[Cl:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH:15]1[C:20]([NH2:21])=[CH:19][CH:18]=[C:17]([OH:22])[CH:16]=1>C(O)C>[Cl:12][C:11]1[C:10](=[O:13])[C:9]2[C:4]([C:3](=[O:14])[C:2]=1[NH:21][C:20]1[CH:15]=[CH:16][C:17]([OH:22])=[CH:18][CH:19]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2,3-Dichloro-1,4-naphthoquinone (1.0 g, 4.4 mmol) was dissolved in 80 ml ethanol at 60° C., to which p-aminophenol (1.44 g, 13.2 mmol) in 20 ml ethanol was added. The reaction mixture was stirred at room temperature for 16 h. The precipitated product was filtered off and recrystallized from ethanol to afford pure purple crystals. Yield: 1.30 g (99%), Mp: 233° C.