CID 66729449 → 1-(Benzyloxy)-3-chloro-7-methoxyisoquinoline

HRID 1520346Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1520346
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[C:4]([Cl:14])[N:3]=1.[CH2:15]([O:22]CC1C=CC=CC=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Na]>C1(C)C=CC=CC=1>[CH2:15]([O:22][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[C:4]([Cl:14])[N:3]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

4

Edukt 2

HCID 66729449CID 66729449HCID 716915371,3-Dichloro-7-methoxyisoquinoline

Produkt 1

HCID 866770731-(Benzyloxy)-3-chloro-7-methoxyisoquinolineAusbeute 84,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

1,3-dichloro-7-methoxyisoquinoline (2.00 g, 8.8 mmol, 1.0 eq.) was dissolved in 30 mL anhydrous toluene and sodium benzyloxide (2.30 g, 17.6 mmol, 2.0 eq.) was added. The mixture was heated to 80° C. for 18 h. TLC indicated the reaction was complete. The mixture was concentrated to give the crude product, which was purified by chromatography on silica gel (eluted with petroleum ether) to give 2.20 g of xxxvii-a as a white solid (84.6%). LCMS m/z=300.1, 302.0 (M+1) (Method B) (retention time=2.23 min).

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. customto give the crude product, which
  3. customwas purified by chromatography on silica gel (eluted with petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-77c1acd2e9434d8b94c3d2c5b96e59fa
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073890B2

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