Diiodomethane → 5-Iodoquinoline

HRID 1955756Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1955756
N[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C(ON=O)CC(C)C.[I:20]CI>>[I:20][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Komponenten

4

Edukt 3

HCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 119115-Aminoquinoline

Produkt 1

HCID 220249805-Iodoquinoline

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A suspension of 10 g (0.07 mol) of 5- aminoquinoline, 94 ml (0.7 mol) of isoamylnitrite and 100 ml of diiodomethane was heated at 80° C. for 2 hours. The reaction mixture was evaporated under reduced pressure at 60°-70° C. The residue was slurried with diethyl ether, decanted and the filtrate was evaporated under reduced pressure. The resulting residue was chromatographed on a silica gel column eluting with 3:1 hexane-ethyl acetate to yield 2.81 g of 5-iodoquinoline. 1H-NMR (CDC13, 300MHz) δ 7.42(d, 1H, J=7.7 Hz); 7.48 (dd, 1H, J=4.3 Hz); 8.1 (m, 2H,); 8.38 (d, 1H, J=8.5 Hz); 8.88 (m, 1H,). Mass spec. m/e=255=p. ##STR27## 2.18 g (0.022 mol) of triethylamine were added to a suspension of 2.75 g (0.011 mol) of 5-iodoquinoline in acetonitrile (24 ml) and the solution formed on warming. The solution was allowed to cool briefly. To the solution were added 50 mg of triphenylphosphine, 50 mg of palladium(II) acetate and 3.1 ml (0.022 mol) of 3,3- zdiethoxy-1-propyne (propiolaldehyde diethylacetal). The reaction was heated at 80° C. for 1.5 hours. The reaction was poured into water and extracted with hexane. The hexane was removed under reduced pressure and the residue was chromatographed on a silica gel column and eluted with 1% methanol-dichloromethane to yield 1.44 g of 5-quinoline-[l- propiolaldehyde diethyl acetal]. 1H-NMR (CDC13, 300MHz) 6 1.3 (t, 6H, J=7.2 Hz); 3.73 (m, 2H,); 3.88 (m, 2H); 5.62 (s, 1H,); 7.48 (dd, IH, J=8.5 and 4.2 Hz); 7.66 (d, 1H, J=7.4 Hz); 7.76 (d, 1H, J=7.2Hz); 8.1 (d, 1H, J=8.5Hz); 8.6 (d, 1H, J=8.5Hz); 8.94 (m, 1H). Mass spec. m/e=255=p. ##STR28##

Aufarbeitung

  1. customThe reaction mixture was evaporated under reduced pressure at 60°-70° C
  2. customdecanted
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe resulting residue was chromatographed on a silica gel column
  5. washeluting with 3:1 hexane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-76218950f8d34629b75f29081617e2ee
Quelldatensatz
uspto-grants-1998_07
Patentnummer
US05776939

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