Ethyl Acetate → 3-Benzoyl-4-(2-methoxyphenylamino)-8-methoxyquinoline

HRID 1382273Notes

Reaction equation

HRID 1382273 reaction equation
[C:1]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1Cl)=[CH:16][CH:15]=[CH:14][C:13]=2[O:20][CH3:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([O:25][CH2:26][CH3:27])(=O)C>O1CCOCC1.COC1C(N)=CC=CC=1>[C:1]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[NH:11][C:10]1[CH:9]=[CH:1][CH:2]=[CH:27][C:26]=1[O:25][CH3:22])=[CH:16][CH:15]=[CH:14][C:13]=2[O:20][CH3:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 100860183-Benzoyl-4-chloro-8-methoxyquinoline

Product 1

HCID 212745583-Benzoyl-4-(2-methoxyphenylamino)-8-methoxyquinolineYield 61%

Reagents, catalysts & solvents 2

HCID 70002-MethoxyanilineSolventHCID 312751,4-DioxaneSolvent

Procedure

3-Benzoyl-4-chloro-8-methoxyquinoline (2.8 g, 0.0094 mol) was heated under reflux in a mixture of 1,4-dioxan (50 ml) and o-anisidine (7 ml) for 1 hour. The solvent was evaporated and the residue was dissolved in dichloromethane, and washed with dilute hydrochloric acid sodium hydrogen carbonate solution, water and brine. The organic solution was dried and evaporated to an oil which was chromatographed (silica gel, 1% methanol in dichloromethane) to give an oil which afforded yellow crystals of 3-benzoyl-4-(2-methoxyphenylamino)-8-methoxyquinoline (2.2 g, 61%) from ethyl acetate, m.p. 200°-202°.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with dilute hydrochloric acid sodium hydrogen carbonate solution, water and brine
  4. customThe organic solution was dried
  5. customevaporated to an oil which
  6. customwas chromatographed (silica gel, 1% methanol in dichloromethane)
  7. customto give an oil which

Sources & evidence

ORD record
ord-065ba7747cde4426948af7c4ab166be0
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

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