Hydrogen Peroxide → 1,2,3,4-Tetrahydro-6-iodoquinoline

HRID 710306Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 710306
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[I:11]I.OO>O>[I:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[NH:1][CH2:2][CH2:3][CH2:4]2

Komponenten

5

Edukt 3

HCID 784Hydrogen PeroxideHCID 807IodineHCID 694601,2,3,4-Tetrahydroquinoline

Produkt 1

HCID 289765451,2,3,4-Tetrahydro-6-iodoquinolineAusbeute 100,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixture of 1,2,3,4,-tetrahydroquinoline (0.34 g; 2.55 mmol) and I2 (0.32 g; 1.27 mmol) in H2O (10 ml), 30% H2O2 (0.26 ml; 2.55 mmol) was added at room temperature. The resulting mixture was vigorously stirred overnight at room temperature, and then extracted with Et2O (2×15 ml). The combined organic phase was washed with H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2; CH2Cl2), to give the title compound (0.33 g; 50%) as a creamy syrup. 1H-NMR (CDCl3) 1.84-1.92 (m, 2H); 2.69 (tr, 2H, J=6.4 Hz); 3.27 (tr, 2H, J=6.4 Hz); 3.82 (broad s, 1H); 6.22 (d, 1H, J=8.2 Hz); 7.15-7.21 (m, 2H).

Aufarbeitung

  1. additionwas added at room temperature
  2. extractionextracted with Et2O (2×15 ml)
  3. washThe combined organic phase was washed with H2O, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure
  7. customthe residue was purified by FCC (SiO2; CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-43265e7603ad43aaa088974e93f33a58
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181182B2

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