Morpholine → 2,4-Dichloro-5-methoxyquinoline

HRID 1852280Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1852280
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][C:6](OC)=[CH:7][CH:8]=2)[N:3]=1.N1CC[O:18][CH2:17]C1.CCN(C(C)C)C(C)C>O1CCOCC1.O>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:18][CH3:17])[N:3]=1

Komponenten

6

Edukt 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 228320542,4-Dichloro-7-methoxyquinoline

Produkt 1

HCID 748913082,4-Dichloro-5-methoxyquinolineAusbeute 60,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a solution of 2,4-dichloro-7-methoxyquinoline (1 g, 4.38 mmol) in 1,4-dioxane (15 ml) was added morpholine (1.9 g, 4.38 mmol) followed by DIPEA (1.7 g, 13.15 mmol) at room temperature. The reaction mass was heated at 140° C. for 18 h. The reaction mass was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get desired compound (0.6 g, 49.1%) as white solid. 1H NMR (400 MHz, CDCl3): δ ppm 7.89-7.86 (d, J=12 Hz, 1H), 7.07 (s, 1H), 6.97-6.94 (d, J=12 Hz, 1H), 6.89 (s, 1H), 3.91 (s, 3H), 3.85-3.82 (m, 4H), 3.69-3.66 (m, 4H); MS: MS m/z 279.1 (M++1).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  3. customevaporated under reduced pressure
  4. customto get crude compound
  5. customThe crude compound was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-107643d6c5b144ca9be19459f48139d5
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957203B2

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