Potassium Iodide → 1-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)-2-(ethyl(methyl)amino)ethanone

HRID 1922458Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1922458
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:15])[CH2:13]Cl)[CH2:7][CH2:6][CH2:5]2.[I-].[K+].[CH3:18][NH:19][CH2:20][CH3:21]>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:15])[CH2:13][N:19]([CH2:20][CH3:21])[CH3:18])[CH2:7][CH2:6][CH2:5]2

Komponenten

6

Edukt 3

HCID 4875Potassium IodideHCID 12219N-MethylethylamineHCID 573433941-(6-Bromo-3,4-dihydro-1(2H)-quinolinyl)-2-chloroethanone

Produkt 1

HCID 573435551-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)-2-(ethyl(methyl)amino)ethanoneAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A suspension of 1-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)-2-chloroethanone (1 g, 3.47 mmol) and potassium iodide (0.115 g, 0.693 mmol) in 10 mL THF was treated with N-methylethanamine (1.786 mL, 20.79 mmol). The mixture was stirred at room temperature for 2 hours then heated at 65° C. for 1 hour. The mixture was concentrated and partitioned between CH2Cl2 (100 mL) and saturated sodium bicarbonate (25 mL). After extraction, the organic layer was separated, dried over Na2SO4, filtered and concentrated to give a light brown residue. This residue was subjected to flash chromatography on silica gel using 5% 2M NH3 in methanol/95% CH2Cl2 to give a light brown residue (1.06 g, 98%). 1H-NMR (CDCl3) δ 7.52-7.40 (br s, 1H), 7.30-7.27 (m, 2H), 3.80 (t, J=6.0 Hz, 2H), 3.28 (s, 2H), 2.72 (t, J=6.9 Hz, 2H), 2.50 (quart, J=7.2 Hz, 2H), 2.30 (s, 3H), 1.96 (quint, J=6.6 Hz, 2H), 1.03 (t, J=7.2 Hz, 3H). MS (ESI): 311.1 and 313.1 (M+1, 100%).

Aufarbeitung

  1. temperaturethen heated at 65° C. for 1 hour
  2. concentrationThe mixture was concentrated
  3. custompartitioned between CH2Cl2 (100 mL) and saturated sodium bicarbonate (25 mL)
  4. extractionAfter extraction
  5. customthe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a light brown residue

Quellen und Nachweise

ORD-Eintrag
ord-2f9d8bcc0b83436fa7ce65605cceeb03
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173813B2

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