Phosphorus oxychloride → HCID 58466468, Verbindung

HRID 2092315Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2092315
[I:1][C:2]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][NH:6][C:7]2=O.P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:7]1[C:8]2[C:3](=[C:2]([I:1])[C:11]([CH3:12])=[CH:10][CH:9]=2)[CH:4]=[CH:5][N:6]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 44479177HCID 44479177, Verbindung

Produkt 1

HCID 58466468HCID 58466468, VerbindungAusbeute 93,9 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

5-Iodo-6-methylisoquinolin-1(2H)-one (2.00 g, 7.02 mmol) was treated with phosphorous oxychloride (6.54 ml, 70.2 mmol) and the mixture stirred at 100° C. for 4 hours. The mixture was cooled and the volatiles removed in vacuo. The residue was taken up in DCM and washed twice with cold water and then twice with saturated aqueous sodium bicarbonate. The organic was dried with sodium sulfate, loaded unto silica and purified by column chromatography on silica gel using 20 to 60% EA in hexanes to give 1-chloro-5-iodo-6-methylisoquinoline (2.00 g, 93.9% yield) as a tan solid. MS (M+H)+ 303.7.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. customthe volatiles removed in vacuo
  3. washwashed twice with cold water
  4. dry with materialThe organic was dried with sodium sulfate
  5. custompurified by column chromatography on silica gel using 20 to 60% EA in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-245787887c8242d1a377dacc23a39b6a
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440674B2

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