4-Amino-2-chlorophenol → HCID 19880280, compound

HRID 1885166Notes

Reaction equation

HRID 1885166 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:16])=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH3:18])(=[O:5])[CH2:2][CH2:3][CH3:4].[Cl:19][C:20]1[CH:25]=[C:24]([NH2:26])[CH:23]=[CH:22][C:21]=1[OH:27]>O1CCOCC1>[ClH:16].[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:26][C:24]1[CH:23]=[CH:22][C:21]([OH:27])=[C:20]([Cl:19])[CH:25]=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 775784-Amino-2-chlorophenolHCID 117775673-Butyryl-4-chloro-8-methoxyquinoline

Product 1

HCID 19880280HCID 19880280, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Butyryl-4-chloro-8-methoxyquinoline (2.64 g, 10 mmol), 2-chloro-4-aminophenol (1.58 g, 11 mmol) and 1,4-dioxan (20 ml) were warmed briefly to reflux, cooled, and the solid filtered off. Recrystallisation from pyridine gave 3-butyryl-4-(3-chloro-4-hydroxyphenylamino)-8methoxyquinoline hydrochloride (1.40 g, 34%), m.p. 267°-269° (dec).

Workup

  1. temperatureto reflux
  2. temperaturecooled
  3. filtrationthe solid filtered off
  4. customRecrystallisation from pyridine

Sources & evidence

ORD record
ord-4865e531a45544a781612cf4e702e660
Source dataset
uspto-grants-1992_09
Patent number
US05143920

Reaction notes

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