Hydrochloric Acid → 1(2H)-Isoquinolinone, 3-methoxy-

HRID 1852072Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1852072
[C:1]([CH2:3][C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[C:6](OC)=[O:7])#[N:2].[CH3:14][O-:15].[Na+].[ClH:17]>CO>[Cl:17][C:6]1[C:5]2[C:4](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:3]=[C:1]([O:15][CH3:14])[N:2]=1.[CH3:14][O:15][C:1]1[NH:2][C:6](=[O:7])[C:5]2[C:4]([CH:3]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 588805Methyl 2-(cyanomethyl)benzoateHCID 10942334Sodium Methoxide

Produkt 2

HCID 122798821(2H)-Isoquinolinone, 3-methoxy-Ausbeute 80 %HCID 222502711-Chloro-3-methoxyisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of methyl 2-(cyanomethyl)benzoate (3.50 g, 20 mmol) and sodium methoxide (10 mL, 25% wt in methanol) in 35 mL MeOH was heated to reflux under nitrogen for 3 h. While still hot, the solution was acidified with 1N HCl solution until the green solution turned to yellow color and a lot of white solid precipitated out. After cooling, the precipitated product was collected by filtration, washed with water and dried to yield the desired product 3-methoxyisoquinolin-1(2H)-one as a white solid (2.8 g, 80%). MS: MS m/z 176.1 (M++1).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for 3 h
  3. customa lot of white solid precipitated out
  4. temperatureAfter cooling
  5. filtrationthe precipitated product was collected by filtration
  6. washwashed with water
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-895f9e6f0b594d9795cdfe368d6de965
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957203B2

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