2-Aminobenzyl alcohol → HCID 10405610, compound

HRID 1090627Notes

Reaction equation

HRID 1090627 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:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][OH:23]>>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][OH:23])=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH3:18])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 214392-Aminobenzyl alcoholHCID 117775673-Butyryl-4-chloro-8-methoxyquinoline

Product 1

HCID 10405610HCID 10405610, compoundYield 53.1%

Procedure

3-Butyryl-4-chloro-8-methoxyquinoline (2.64 g, 10 mmol) was dissolved in I,4-dioxan (10 ml), 2-aminobenzyl alcohol (1.85 g, I5 mmol) added, and the mixture heated to reflux for 5 minutes. The dioxan was evaporated, water added, and the product extracted into dichloromethane. Chromatography (silica gel, ethyl acetate) and recrystallisation from ethyl acetate gave 3-butyryl-4-(2-(hydroxymethyl)phenylamino)-8-methoxyquinoline (1.86 g, 53%), m.p. 159°-161°.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 5 minutes
  3. customThe dioxan was evaporated
  4. additionwater added
  5. extractionthe product extracted into dichloromethane
  6. customChromatography (silica gel, ethyl acetate) and recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-190918d037d548669f5ea4469b82e8df
Source dataset
uspto-grants-1992_01
Patent number
US05082848

Reaction notes

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