2-Methoxyaniline → 3-Butyryl-4-(2-methoxyphenylamino)-8-methoxyquinoline

HRID 1382283Notes

Reaction equation

HRID 1382283 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].[CH3:19][O:20][C:21]1[C:22]([NH2:27])=[CH:23][CH:24]=[CH:25][CH:26]=1>O1CCOCC1>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[O:20][CH3:19])=[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 70002-MethoxyanilineHCID 117775673-Butyryl-4-chloro-8-methoxyquinoline

Product 1

HCID 100207823-Butyryl-4-(2-methoxyphenylamino)-8-methoxyquinolineYield 68.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Butyryl-4-chloro-8-methoxyquinoline (20.2 g, 0.077 mol) and o-anisidine (15 ml, 0.11 mol) were heated under reflux in 1,4-dioxan (150 ml) for 1 hour. The solvent was evaporated and the residue dissolved in dichloromethane and washed with dilute hydrochloric acid, sodium bicarbonate solution and brine. The solution was dried, filtered and evaporated to a yellow solid, which was triturated with ether to give 3-butyryl-4-(2-methoxyphenylamino)-8-methoxyquinoline (18.55 g, 68.75%) m.p. 159°-161°.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in dichloromethane
  3. washwashed with dilute hydrochloric acid, sodium bicarbonate solution and brine
  4. customThe solution was dried
  5. filtrationfiltered
  6. customevaporated to a yellow solid, which
  7. customwas triturated with ether

Sources & evidence

ORD record
ord-10171ce42757473587dc7ed7dc3fd6e7
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

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