Methanol → 1-Methoxy-5-nitroisoquinoline

HRID 1645912

Reaktionsgleichung

Reaktionsgleichung von HRID 1645912
[Na].Cl[C:3]1[C:12]2[C:7](=[C:8]([N+:13]([O-:15])=[O:14])[CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][N:4]=1.[CH3:16][OH:17]>>[CH3:16][O:17][C:3]1[C:12]2[C:7](=[C:8]([N+:13]([O-:15])=[O:14])[CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][N:4]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 4597741-Chloro-5-nitroisoquinolineHCID 5360545Sodium

Produkt 1

HCID 8306811-Methoxy-5-nitroisoquinoline

Versuchsvorschrift

To a solution of 1.0 g of sodium (43.4 mmol) in methanol was added 1.42 g (6.8 mmol) of 1-chloro-5-nitroisoquinoline. The mixture was heated under reflux for three hours, cooled, and concentrated. The residue was partitioned between water and methylene chloride, dried, and filtered through SiO2. The filtrate was concentrated to give 1.3 g of the 1-methoxy-5-nitroisoquinoline. This material was suspended in 150 ml of methanol, 0.3 g of 5% Pd-C was added, and the mixture was hydrogenated at room temperature for 18 hours. The mixture was filtered and concentrated. The residue was crystallized from ether/hexane to give 0.32 g (27%) of the desired product; mp 53°-57°.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for three hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. customThe residue was partitioned between water and methylene chloride
  6. customdried
  7. filtrationfiltered through SiO2
  8. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-d5db6b2f2661446bab1d2b4b9d2e616c
Quelldatensatz
uspto-grants-1993_01
Patentnummer
US05177075

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