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

HRID 1382256Notes

Reaction equation

HRID 1382256 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-15386ba092444e1186200b22270b956f
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

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