HCID 86696916, Verbindung → 7-(3-Chloropropoxy)-6-methoxyquinolin-4-OL

HRID 1049061Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1049061
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([C:14](=[O:20])/[CH:15]=[CH:16]/N(C)C)=[C:8]([N+:21]([O-])=O)[CH:7]=1>C(O)(=O)C.[Fe]>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:9]([C:14](=[O:20])[CH:15]=[CH:16][NH:21]2)=[CH:10][C:11]=1[O:12][CH3:13]

Komponenten

4

Edukt 1

HCID 86696916HCID 86696916, Verbindung3×

Produkt 1

HCID 717440127-(3-Chloropropoxy)-6-methoxyquinolin-4-OLAusbeute 67,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

0.44 moL of (E)-1-(4-(3-Chloropropoxy)-5-methoxy-2-nitrophenyl)-3-(dimethylamino)prop-2-en-1-one (intermediate IV) (150 g) was dissolved in 1200 mL of glacial acetic acid (8 v/w), and the mixture was heated to 40° C. After intermediate IV was completely dissolve, 2.20 mol (123.1 g) Iron powder was added slowly, then the reaction mixture was heated to 80° C. with mechanical stirring for 2 h. After completion of the reaction, the reaction mixture was filtered immediately to remove iron powder. The filtrate was collected and cooled to precipitate solid, and then filtered to give yellow solid, which was dissolved in glacial acetic acid and the solution was stirred at 80° C. for 30 min then filtered immediately again. The filtrate was cooled to precipitate solid, filtered, and the filter cake was washed with water until the aqueous layer became neutral, dried to give solid 79 g. Yield: 65%.

Aufarbeitung

  1. temperaturethe reaction mixture was heated to 80° C.
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture was filtered immediately
  4. customto remove iron powder
  5. customThe filtrate was collected
  6. temperaturecooled
  7. customto precipitate solid
  8. filtrationfiltered
  9. customto give yellow solid, which
  10. stirringthe solution was stirred at 80° C. for 30 min
  11. filtrationthen filtered immediately again
  12. temperatureThe filtrate was cooled
  13. customto precipitate solid
  14. filtrationfiltered
  15. washthe filter cake was washed with water until the aqueous layer
  16. customdried

Quellen und Nachweise

ORD-Eintrag
ord-bb1a1ddfea874552b0d771e987bf5618
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09382232B2

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