N,N-Dimethylaniline → Ethyl 4-chloro-3,6-dimethylquinoline-2-carboxylate

HRID 1604544Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1604544
[CH3:1][C:2]1[C:11](=O)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH3:13])[CH:9]=2)[NH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].P(Cl)(Cl)([Cl:21])=O.CN(C)C1C=CC=CC=1>>[Cl:21][C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH3:13])[CH:9]=2)[N:4]=[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:2]=1[CH3:1]

Komponenten

4

Edukt 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 19603453Ethyl 1,4-dihydro-3,6-dimethyl-4-oxoquinoline-2-carboxylate

Produkt 1

HCID 19603353Ethyl 4-chloro-3,6-dimethylquinoline-2-carboxylateAusbeute 73,7 %

Versuchsvorschrift

To a mixture of ethyl 1,4-dihydro-3,6-dimethyl-4-oxoquinoline-2-carboxylate (4.0 g) and phosphoryl chloride (10 g) was added N,N-dimethylaniline (3.95 g) at ambient temperate and the mixture was stirred for 1 hour. The solvent was removed in vacuo, and the residue was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with water, saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (n-hexane-dichloromethane) to give ethyl 4-chloro-3,6-dimethylquinoline-2-carboxylate (3.17 g) as an oil.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. additionthe residue was poured into ice-water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, saturated sodium bicarbonate solution and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (n-hexane-dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-fc1cfc469f314395af64c28708098622
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05994368

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