4-Aminophenol → 1,4-Naphthalenedione, 2-chloro-3-((4-hydroxyphenyl)amino)-

HRID 1895501Notes

Reaction equation

HRID 1895501 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]=2

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 8342Dichlone

Product 1

HCID 2605561,4-Naphthalenedione, 2-chloro-3-((4-hydroxyphenyl)amino)-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

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.

Workup

  1. additionwas added
  2. filtrationThe precipitated product was filtered off
  3. customrecrystallized from ethanol
  4. customto afford pure purple crystals

Sources & evidence

ORD record
ord-6127ee6e063b43549b10842add879073
Source dataset
uspto-grants-2013_08
Patent number
US08513437B2

Reaction notes

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