O-Toluidine → 3-Butyryl-4-(2-methylphenylamino)-8-methoxyquinoline

HRID 1382260Notes

Reaction equation

HRID 1382260 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[C:21]([CH3:26])=[CH:22][CH:23]=[CH:24][CH:25]=1>O1CCOCC1>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:26])=[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 7242O-ToluidineHCID 117775673-Butyryl-4-chloro-8-methoxyquinoline

Product 1

HCID 30810873-Butyryl-4-(2-methylphenylamino)-8-methoxyquinoline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-butyryl-4-chloro-8-methoxyquinoline (6.0 g, 023 mol) and o-toluidine (6.0 ml, 0.056 mol) in 1,4-dioxan (100 ml) was heated under reflux with stirring for 1 hour. The mixture was evaporated and chromatographed (silica gel, 2% methanol in dichloromethane) to give 3-butyryl-4-(2-methylphenylamino)-8-methoxyquinoline as an oil which was isolated as the hydrochloride salt (2.12 g, 25.1%), m.p. 215°-217° by crystallisation from ethyl acetate and then recrystallisation from acetone.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customThe mixture was evaporated
  4. customchromatographed (silica gel, 2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-d6c08a323cd440ef90f3307ec4f7de23
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

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