Acetic Acid → 3-iodo-1H-quinolin-2-one

HRID 585013Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 585013
Cl[C:2]1[C:11]([I:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(O)(=[O:15])C>O>[I:12][C:11]1[C:2](=[O:15])[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Komponenten

4

Edukt 2

HCID 176Acetic AcidHCID 146166232-Chloro-3-iodoquinoline

Produkt 1

HCID 114145753-iodo-1H-quinolin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

The 2-chloro-3-iodoquinoline (1-2, 30.0 g) was weighed into a 250 mL flask and suspended in of 50% aqueous acetic acid (125 mL). The mixture was heated to 100° C. and allowed to reflux for 16 hours to completion by TLC analysis of the crude reaction mixture. The mixture was allowed to cool to ambient temperature followed by dilution with 200 mL of water. The desired product was isolated by vacuum filtration followed by washing with water (50 mL). The water and traces of acetic acid were removed under vacuum for 5 hours to afford the desired quinolinone as a tan powder (1-3); 1H NMR (500 MHz, CDCl3) δ 12.13 (br s, 1H), 8.71 (s, 1H), 7.65 (d, 1H, J=7.5 Hz), 7.54 (m, 1H), 7.31 (d, 1H, J=8.0 Hz), 7.20 (m, 1H).

Aufarbeitung

  1. temperatureto reflux for 16 hours to completion by TLC analysis of the crude
  2. customreaction mixture
  3. temperatureto cool to ambient temperature

Quellen und Nachweise

ORD-Eintrag
ord-117052848c894393995237a75ddf27e0
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06927293B2

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