Triethylamine → Quinoline-6-carbonitrile

HRID 876792

Reaktionsgleichung

Reaktionsgleichung von HRID 876792
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH2:13])=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]#[N:13])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 11052097Quinoline-6-carboxamide

Produkt 1

HCID 592995Quinoline-6-carbonitrileAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a mixture of quinoline-6-carboxamide (0-3) (1.2 g, 7.2 mmol) and triethylamine (2.2 g, 21.8 mmol) in DCM (50 mL) at 0° C. was added trifluoroacetic acid anhydride (1.9 g, 8.9 mmol). The reaction was stirred for 10 mins at 0° C., then quenched with water. The resulting mixture was extracted with DCM. The organic layer was dried over anhydrous Na2SO4, and concentrated to afford the desired title compound (1.0 g). MS (m/z): 154 (M)+.

Aufarbeitung

  1. customquenched with water
  2. extractionThe resulting mixture was extracted with DCM
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-afe968d3ef0340db91325a91e1947b50
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987269B2

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