Potassium Carbonate → methyl 2-{4-[N-(6-chloro-2-quinolinyl)-N-methylamino]-phenoxy}propionate

HRID 326048Notes

Reaction equation

HRID 326048 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[CH3:13])[CH:6]=[CH:5]2.Br[CH:22]([CH3:27])[C:23]([O:25][CH3:26])=[O:24].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH:22]([CH3:27])[C:23]([O:25][CH3:26])=[O:24])=[CH:16][CH:15]=1)[CH3:13])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionateHCID 204619604-[N-(6-chloro-2-quinolinyl)-N-methylamino]phenol

Product 1

HCID 20461952methyl 2-{4-[N-(6-chloro-2-quinolinyl)-N-methylamino]-phenoxy}propionate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-[N-(6-chloro-2-quinolinyl)-N-methylamino]phenol (1.1 g), methyl 2-bromopropionate (1.3 ml), anhydrous potassium carbonate (0.7 g) and acetone (20 ml) was heated under reflux with stirring for a period of 16 hours. The acetone was removed by distillation under reduced pressure and the residue was partitioned between water and chloroform. The chloroform extracts were dried (anhydrous MgSO4) and the solvent was evaporated. The residue was chromatographed over silica gel (40 g) with chloroform elution to give methyl 2-{4-[N-(6-chloro-2-quinolinyl)-N-methylamino]-phenoxy}propionate (1.05 g) as a colourless oil. Proton magnetic resonance spectrum (CDCl3 ; δ ppm); 8.0-6.6 (9H, m, quinoline and phenoxy protons); 4.9 (1H, q, CH--CH3); 3.9 (3H, s, OCH3); 3.6 (3H, s, N--CH3); 1.6 (3H, d, CHCH3).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customThe acetone was removed by distillation under reduced pressure
  4. customthe residue was partitioned between water and chloroform
  5. dry with materialThe chloroform extracts were dried (anhydrous MgSO4)
  6. customthe solvent was evaporated
  7. customThe residue was chromatographed over silica gel (40 g) with chloroform elution

Sources & evidence

ORD record
ord-737c422981d1403280fc4fb038e5e499
Source dataset
uspto-grants-1984_04
Patent number
US04444584

Reaction notes

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