Sodium Bicarbonate → 4-Chloro-6-iodo-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline

HRID 928823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 928823
Cl[C:2]1[C:11]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)=[C:10]([Cl:23])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([I:24])[CH:8]=2)[N:3]=1.C[O-].[Na+].[C:28](=O)(O)[O-:29].[Na+]>C1(C)C=CC=CC=1>[Cl:23][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([I:24])[CH:8]=2)[N:3]=[C:2]([O:29][CH3:28])[C:11]=1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 867156552,4-Dichloro-6-iodo-3-(4-(trifluoromethyl)benzyl)quinoline2×

Produkt 1

HCID 867156544-Chloro-6-iodo-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
92 °C

Versuchsvorschrift

A heterogeneous mixture of 2,4-dichloro-6-iodo-3-(4-(trifluoromethyl)benzyl)quinoline (515 g, 1.068 mol, Intermediate 62: step b) and sodium methoxide (577.1 g, 10.68 mol) in toluene (5.34 L) was heated to 92° C. for 18 h and then 100° C. for 13 h. After cooling to room temperature the slurry was poured over an aqueous solution of sodium bicarbonate (11.54 kg, 7 wt %, 9.615 mol). The biphasic system was mixed and then the layers were separated. The organic layer was dried over MgSO4, filtered, and concentrated to afford the title compound as a white solid.

Aufarbeitung

  1. temperatureAfter cooling to room temperature the slurry
  2. additionThe biphasic system was mixed
  3. customthe layers were separated
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-72a19a1e21db432db9915ab5c957991c
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290476B2

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