Reaktion #590822

Reaktionsgleichung

N-(4-(6-nitroquinolin-4-ylthio)phenyl)-4-phenylphthalazin-1-amine

tin (II) chloride

water

→

N-(4-(6-aminoquinolin-4-ylthio)phenyl)-4-phenylphthalazin-1-amine

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter 15 minutes of sonication
2. 2
   Sonstigewater was removed under vacuum azeotropically with benzene
3. 3
   workup.ADDITIONDCM was added to the suspension
4. 4
   SonstigeYellow solids precipitated out of the solution
5. 5
   Filtrationwere filtered off with DCM
6. 6
   EinengenThe filtrate was concentrated
7. 7
   Sonstigepurified by RPLC on an acidic Gilson column system
8. 8
   workup.ADDITIONFractions containing the product
9. 9
   Waschenwere washed with sat. NaHCO3
10. 10
    ExtraktionThe product was extracted with DCM
11. 11
    WaschenThe organic was washed with brine
12. 12
    Trocknendried over MgSO4
13. 13
    Filtrationfiltered
14. 14
    Einengenconcentrated
15. 15
    SonstigeThe product was purified further

Vorschrift

To a solution of N-(4-(6-nitroquinolin-4-ylthio)phenyl)-4-phenylphthalazin-1-amine (228 mg, 455 μmol) in 1 mL of DMF, was added tin (II) chloride (431 mg, 2273 μmol) and 115 uL of water. After 15 minutes of sonication, the reaction was stirred at rt. After 2 days, water was removed under vacuum azeotropically with benzene. DCM was added to the suspension. Yellow solids precipitated out of the solution and were filtered off with DCM. The filtrate was concentrated and purified by RPLC on an acidic Gilson column system. Fractions containing the product were washed with sat. NaHCO3. The product was extracted with DCM. The organic was washed with brine, dried over MgSO4, filtered, and concentrated. The product was purified further by performing a column chromatography using 60:40 DCM:(90:10:1 DCM:MeOH:NH4OH). Yellow solid, N-(4-(6-aminoquinolin-4-ylthio)phenyl)-4-phenylphthalazin-1-amine was obtained.

Quelle