Acetamide → 6-Chloroquinolin-2-amine

HRID 514858Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 514858
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:12])[CH:8]=2)[N:3]=1.C([NH2:16])(=O)C.C([O-])([O-])=O.[K+].[K+]>>[Cl:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH2:16])[CH:11]=[CH:10]2

Komponenten

4

Edukt 3

HCID 178AcetamideHCID 11430Potassium CarbonateHCID 6075022,6-Dichloroquinoline2×

Produkt 1

HCID 140674256-Chloroquinolin-2-amineAusbeute 98,5 %

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

A mixture of 2,6-dichloroquinoline (500 mg, 2.5 mmol), acetamide (3 g, 50.8 mmol) and K2CO3 (1.75 g, 12.7 mmol) in a round bottom flask was stirred at 200° C. for 1.5 hours until TLC indicated that 2,6-dichloroquinoline was consumed. The resulting mixture was cooled to room temperature, and was partitioned between dichloromethane and H2O, the organic layer was dried over anhydrous Na2SO4, concentrated, and the residue was purified by a standard method to give 440 mg of the title compound. LCMS (m/z): 179.7 (M+1)+

Aufarbeitung

  1. customwas consumed
  2. temperatureThe resulting mixture was cooled to room temperature
  3. customwas partitioned between dichloromethane and H2O
  4. dry with materialthe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customthe residue was purified by a standard method

Quellen und Nachweise

ORD-Eintrag
ord-f129f5d84519442e989db335c55789f1
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108921B2

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