4-Amino-2,6-dimethylphenol → 3-Butyryl-4-(3,5-dimethyl-4-hydroxyphenylamino)-8-methoxyquinoline

HRID 1885180Notes

Reaction equation

HRID 1885180 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[C:11]([C:16]1[CH:17]=[N:18][C:19]2[C:24]([C:25]=1Cl)=[CH:23][CH:22]=[CH:21][C:20]=2[O:27][CH3:28])(=[O:15])[CH2:12][CH2:13][CH3:14]>O1CCOCC1>[C:11]([C:16]1[CH:17]=[N:18][C:19]2[C:24]([C:25]=1[NH:8][C:6]1[CH:7]=[C:2]([CH3:1])[C:3]([OH:10])=[C:4]([CH3:9])[CH:5]=1)=[CH:23][CH:22]=[CH:21][C:20]=2[O:27][CH3:28])(=[O:15])[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 826684-Amino-2,6-dimethylphenolHCID 117775673-Butyryl-4-chloro-8-methoxyquinoline

Product 1

HCID 99988643-Butyryl-4-(3,5-dimethyl-4-hydroxyphenylamino)-8-methoxyquinolineYield 60.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2,6-Dimethyl-4-aminophenol (0.78 g, 5.69 mmol) and 3-butyryl-4-chloro-8-methoxyquinoline (1.0 g, 3.79 mmol) in dioxan (35 ml) were refluxed under nitrogen for 2.5 hours. The solvent was evaporated, and the residue treated with saturated sodium bicarbonate solution and chloroform. The resulting solid was filtered, washed with chloroform and water, boiled in methanol and filtered again to give the title compound (0.84 g) m.p. 287°-9° (dec).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue treated with saturated sodium bicarbonate solution and chloroform
  3. filtrationThe resulting solid was filtered
  4. washwashed with chloroform and water
  5. filtrationfiltered again

Sources & evidence

ORD record
ord-e21762c4f2bd48509015d8c3d8c068a6
Source dataset
uspto-grants-1992_09
Patent number
US05143920

Reaction notes

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