1,2-Dichloroethane → Quinoline

HRID 53654

Reaktionsgleichung

Reaktionsgleichung von HRID 53654
[CH:1]1[CH:6]=[C:5]2[CH:7]=[CH:8][C:9](C(O)=O)=[N:10][C:4]2=[CH:3][CH:2]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[N:10]1[C:4]2[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=2)[CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 111,2-DichloroethaneHCID 7124Quinaldic AcidHCID 757711-Hydroxybenzotriazole

Produkt 1

HCID 7047QuinolineAusbeute 319,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A 100 ml RBF equipped with magnetic stir bar and N2 inlet was charged with 356 mg (2.06 mmol, 1 eq) 2-quinaldic acid in 10 ml dry DMF. The solution was cooled to 0° C. and 415 mg (3.07 mmol, 1.5 eq) HOBt was added followed by 415 mg EDC (2.16 mmol, 1.05 eq). The reaction was stirred 2 hours at 0° C. when 1.1 g (2.06 mmol, 1 eq) of free asparagine amine in 10 ml dry DMF was added. The reaction was stirred at 0° C. for 2 hours then room temperature overnight. The reaction was poured into sat. bicarb and extracted with 2×65 mL ethyl acetate. The combined organics were washed with 5% aq. citric acid, brine, dried and concentrated to 1.4 g crude foam. Purification by flash chromatography on silica gel (100% ethyl acetate) yielded 850 mg (61%) of quinoline adduct.

Aufarbeitung

  1. customA 100 ml RBF equipped with magnetic stir bar and N2 inlet
  2. additionwas added
  3. customroom temperature overnight
  4. additionThe reaction was poured into sat. bicarb
  5. extractionextracted with 2×65 mL ethyl acetate
  6. washThe combined organics were washed with 5% aq. citric acid, brine
  7. customdried
  8. concentrationconcentrated to 1.4 g crude foam
  9. customPurification by flash chromatography on silica gel (100% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-2418f6fa7a6540388b5cd366afeeca75
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05620977

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