4-Aminophenol → 4-[(7-chloroquinolin-4-yl)amino]phenol

HRID 1190891Notes

Reaction equation

HRID 1190891 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[C:10]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[N:13]=[CH:12][CH:11]=1>C(O)C>[Cl:20][C:16]1[CH:15]=[C:14]2[C:19]([C:10]([NH:1][C:2]3[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=3)=[CH:11][CH:12]=[N:13]2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 68664,7-Dichloroquinoline

Product 1

HCID 2241784-[(7-chloroquinolin-4-yl)amino]phenolYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Aminophenol (1.09 g, 10 mmol) and 4,7-dichloroquinoline (1.98 g, 1 eq) were refluxed in 50 mL of ethanol for 2 h. The reaction mixture was then cooled to room temperature and the precipitate was removed by filtration and washed successively with a saturated aqueous solution of NaHCO3, water, methanol and then petroleum ether to yield expected compound as a yellow powder (2.57 g, 95% yield). m/z (ESI) 271.1 [M+H]+.

Workup

  1. customthe precipitate was removed by filtration
  2. washwashed successively with a saturated aqueous solution of NaHCO3, water, methanol

Sources & evidence

ORD record
ord-93e91897916f4043988484d4943f0ac5
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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