O-Toluidine → 1-[8-methoxy-4-(2-methylanilino)quinolin-3-yl]ethanone

HRID 1382308Notes

Reaction equation

HRID 1382308 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1Cl)=[CH:11][CH:10]=[CH:9][C:8]=2[O:15][CH3:16])(=[O:3])[CH3:2].[NH2:17][C:18]1[C:19]([CH3:24])=[CH:20][CH:21]=[CH:22][CH:23]=1>O1CCOCC1>[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24])=[CH:11][CH:10]=[CH:9][C:8]=2[O:15][CH3:16])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 100143131-(4-Chloro-8-methoxy-3-quinolinyl)ethanone

Product 1

HCID 104704091-[8-methoxy-4-(2-methylanilino)quinolin-3-yl]ethanoneYield 45.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of crude 3-acetyl-4-chloro-8-methoxyquinoline (7.9 g) and o-toluidine (2 ml, 19 mmol) in dioxan (150 ml) was heated under reflux with stirring for 2 hours, then cooled and evaporated. Aqueous sodium bicarbonate was added, the mixture extracted with chloroform, and the organic extract dried and evaporated. Recrystallisation from ethyl acetate and then from ethanol gave 3-acetyl-4-(2-methylphenylamino)-8-methoxyquinoline (2.65 g, 44% from 3-acetyl-8-methoxy-4(1H)-quinolone), m.p. 171°-173°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperaturecooled
  4. customevaporated
  5. additionAqueous sodium bicarbonate was added
  6. extractionthe mixture extracted with chloroform
  7. extractionthe organic extract
  8. customdried
  9. customevaporated
  10. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-c48f1d25b087454ebb7a5edd3937a0aa
Source dataset
uspto-grants-1989_02
Patent number
US04806550

Reaction notes

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