Nitric Acid → 3-Methyl-5-nitroisoquinoline

HRID 1181404

Reaktionsgleichung

Reaktionsgleichung von HRID 1181404
[CH3:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.OS(O)(=O)=O.[N+:17]([O-])([OH:19])=[O:18].[OH-].[Na+]>CO>[CH3:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([N+:17]([O-:19])=[O:18])[CH:8]=[CH:7][CH:6]=2

Komponenten

6

Edukt 4

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 143063-MethylisoquinolineHCID 14798Sodium Hydroxide

Produkt 1

HCID 2749733-Methyl-5-nitroisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

3-Methylisoquinoline (2.14 g, 14.9 mmol) was added portionwise to ice-cooled concentrated H2SO4 (10 ml) keeping the internal temperature below 10° C. A nitrating mixture of concentrated H2SO4 (2 ml) and fuming nitric acid (2 ml) was then added dropwise keeping the internal temperature below 15° C. After stirring for 30 minutes, TLC indicated reaction was complete. The acid was neutralized by adding the mixture to an excess of 4N aqueous NaOH (180 ml) with ice-cooling. The mixture was extracted with dicbloromethane (2×150 ml), then dried (Na2SO4) and evaporated to give the crude product (2.69 g) as a yellow solid. Flash column chromatography using as eluant 5% methanol in dicbloromethane gave a pure sample of the title compound (660 mg) and a further sample (1.95 g) containing ca. 10% of the isomer 3-methyl-8-nitroisoquinoline.

Aufarbeitung

  1. customthe internal temperature below 10° C
  2. additionwas then added dropwise
  3. customthe internal temperature below 15° C
  4. customreaction
  5. temperaturecooling
  6. extractionThe mixture was extracted with dicbloromethane (2×150 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customto give the crude product (2.69 g) as a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-4399df6bad6d44aca6b570e32076d5c5
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07285563B2

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