4-Aminophenol → HCID 10337083, compound

HRID 1885162Notes

Reaction equation

HRID 1885162 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH3:18])(=[O:5])[CH2:2][CH2:3][CH3:4].[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1>O1CCOCC1>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH3:18])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 117775673-Butyryl-4-chloro-8-methoxyquinoline

Product 1

HCID 10337083HCID 10337083, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Butyryl-4-chloro-8-methoxyquinoline (2 g, 8 mmol), 4-aminophenol (1.24 g, 11 mmol) and 1,4-dioxan (50 ml) were heated at reflux for 2 hours, then the solid filtered off and converted to free base. Recrystallisation from ethanol and then methanol gave 3-butyryl-4-(4-hydroxyphenylamino)-8-methoxyquinoline (1.6 g), m.p. 270°-272°.

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationthe solid filtered off
  3. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-e6043cd61ec14f2c886d5d7ab3aa442b
Source dataset
uspto-grants-1992_09
Patent number
US05143920

Reaction notes

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