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Dimethylformamide → Methyl 6-[(4,6-Dimethoxypyrimidin-2-yl)oxy]quinolin-5-carboxylate

HRID 52008
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 52008
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:3]=1[C:12]([O:14][CH3:15])=[O:13].[CH3:16][O:17][C:18]1[CH:23]=[C:22]([O:24][CH3:25])[N:21]=[C:20](S(C)(=O)=O)C=1.C(=O)([O-])[O-].[K+].[K+].C[N:37](C)C=O>>[CH3:16][O:17][C:18]1[CH:23]=[C:22]([O:24][CH3:25])[N:21]=[C:20]([O:1][C:2]2[CH:11]=[CH:10][C:9]3[N:8]=[CH:7][CH:6]=[CH:5][C:4]=3[C:3]=2[C:12]([O:14][CH3:15])=[O:13])[N:37]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 19077292Methyl 6-hydroxyquinoline-5-carboxylateHCID 190772944,6-Dimethoxy-2-methylsulfonylpyridine

Produkt 1

HCID 19962792Methyl 6-[(4,6-Dimethoxypyrimidin-2-yl)oxy]quinolin-5-carboxylateAusbeute 89 %

Versuchsvorschrift

0.8 g of methyl 6-hydroxyquinolin-5-carboxylate, 0.96 g of 4,6-dimethoxy-2-methylsulfonylpyridine and 0.82 g of potassium carbonate were stirred in 30 ml of N,N-dimethylformamide at 80° C. for 3 hours. The mixture was returned to room temperature, then poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from a solvent mixture of dichloromethane/isopropyl ether to obtain 1.21 g (yield: 89.0%) of the desired compound. mp: 160°-162° C.

Aufarbeitung

  1. customwas returned to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe residue obtained by concentration under reduced pressure
  6. customwas crystallized from a solvent mixture of dichloromethane/isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-e43d90e1663e4fddb1a11532e7b30547
Quelldatensatz
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05616537

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