Potassium Hydroxide → 1-Methyl-7-nitro-3,4-dihydroisoquinoline

HRID 650950

Reaktionsgleichung

Reaktionsgleichung von HRID 650950
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][N:3]=1.[N+:12]([O-])([O-:14])=[O:13].[K+].[OH-].[K+]>S(=O)(=O)(O)O>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[CH2:5][CH2:4][N:3]=1

Komponenten

5

Edukt 3

HCID 14797Potassium HydroxideHCID 24434Potassium NitrateHCID 2315021-Methyl-3,4-dihydroisoquinoline

Produkt 1

HCID 109322281-Methyl-7-nitro-3,4-dihydroisoquinolineAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of (±) 1-methyl-3,4-dihydroisoquinoline (2.57 g, 17.7 mmol) in conc. sulfuric acid (10 ml) was added dropwise to a stirred mixture of potassium nitrate (1.93 g, 19.1 mmol) in conc. sulfuric acid (10 ml) at −5° C. The mixture was allowed to reach room temperature over 2 h and then heated at 60° C. for 4 h. The reaction mixture was poured into ice-water (100 ml) and basified (pH 9) with KOH pellets. Extraction into dichloromethane (3×50 ml), drying over anhydrous sodium sulfate and evaporation in vacuo yielded the crude product. Purification by chromatography through silica gel, eluting with (0.5% 0.88 NH3: 4.5% CH3OH: 95% CH2Cl2) afforded the title compound as a dark brown oil (1.92 g, 57%).

Aufarbeitung

  1. extractionExtraction into dichloromethane (3×50 ml)
  2. dry with materialdrying over anhydrous sodium sulfate and evaporation in vacuo
  3. customyielded the crude product
  4. customPurification by chromatography through silica gel
  5. washeluting with (0.5% 0.88 NH3: 4.5% CH3OH: 95% CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-462cb86d6c2e47d2b6d3ab989d24a4ef
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06277861B1

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