(3-Amino-4-methylphenyl)methanol → 3-Butyryl-4-(5-hydroxymethyl-2-methylphenylamino)-8-methoxyquinoline

HRID 1090636Notes

Reaction equation

HRID 1090636 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:21]=[C:22]([CH:25]=[CH:26][C:27]=1[CH3:28])[CH2:23][OH:24]>O1CCOCC1>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:19][C:20]1[CH:21]=[C:22]([CH2:23][OH:24])[CH:25]=[CH:26][C:27]=1[CH3:28])=[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 586243(3-Amino-4-methylphenyl)methanolHCID 117775673-Butyryl-4-chloro-8-methoxyquinoline

Product 1

HCID 104739643-Butyryl-4-(5-hydroxymethyl-2-methylphenylamino)-8-methoxyquinolineYield 59.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-butyryl-4-chloro-8-methoxyquinoline (0.80 g, 3 mmol) and 3-amino-4-methylbenzyl alcohol (0.48 g, 3.5 mmol) in dioxan (I0 ml) was heated at reflux for 1.5 hours, then the solvent evaporated. Aqueous sodium bicarbonate was added, the product extracted into dichloromethane, dried and evaporated. Recrystallisation from methanol gave 3-butyryl-4-(5-hydroxymethyl-2-methylphenylamino)-8-methoxyquinoline (0.65 g, 59%) 180°-181°.

Workup

  1. temperatureat reflux for 1.5 hours
  2. customthe solvent evaporated
  3. additionAqueous sodium bicarbonate was added
  4. extractionthe product extracted into dichloromethane
  5. customdried
  6. customevaporated
  7. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-328c7b6a7c3b4916adbdfc00a528935d
Source dataset
uspto-grants-1992_01
Patent number
US05082848

Reaction notes

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