5-Bromo-2-methyl-8-nitro-1,2,3,4-tetrahydroisoquinoline → 2-Methyl-1,2,3,4-tetrahydroisoquinolin-8-amine

HRID 641925Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 641925
Br[C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:15])[CH2:7]2>[Pd]>[CH3:15][N:6]1[CH2:5][CH2:4][C:3]2[C:8](=[C:9]([NH2:12])[CH:10]=[CH:11][CH:2]=2)[CH2:7]1

Komponenten

3

Edukt 1

HCID 100160105-Bromo-2-methyl-8-nitro-1,2,3,4-tetrahydroisoquinoline

Produkt 1

HCID 135299172-Methyl-1,2,3,4-tetrahydroisoquinolin-8-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

Into a 250 mL 3-necked round bottom flask was added a solution of 5-bromo-2-methyl-8-nitro-1,2,3,4-tetrahydroisoquinoline (4.85 g, 17.89 mmol) in CH3OH/Et3N(anhydrous) (150/15 mL). To the mixture was added Pd/C (4.5 g). Hydrogen gas was bubbled into the mixture The resulting solution was allowed to react, with stirring, for 3 hours while the temperature was maintained at room temperature. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:1). A filtration was performed. The filtrate was concentrated by evaporation under vacuum using a rotary evaporator. The resulting solution was diluted with 50 mL of Na2CO3 (10%). The resulting solution was extracted four times with 50 mL of ethyl acetate and the organic layers combined and dried over Na2SO4. The residue was purified by eluting through a column with a 50:1 CH2Cl2/MeOH solvent system. This resulted in 2.57 g (89%) of 2-methyl-1,2,3,4-tetrahydroisoquinolin-8-amine as a light yellow oil.

Aufarbeitung

  1. customHydrogen gas was bubbled into the mixture The resulting solution
  2. customto react
  3. filtrationA filtration
  4. concentrationThe filtrate was concentrated by evaporation under vacuum
  5. customa rotary evaporator
  6. additionThe resulting solution was diluted with 50 mL of Na2CO3 (10%)
  7. extractionThe resulting solution was extracted four times with 50 mL of ethyl acetate
  8. dry with materialdried over Na2SO4
  9. customThe residue was purified
  10. washby eluting through a column with a 50:1 CH2Cl2/MeOH solvent system
  11. customThis resulted in 2.57 g (89%) of 2-methyl-1,2,3,4-tetrahydroisoquinolin-8-amine as a light yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-d586a017d530495b9fd6823ab03de23c
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696229B2

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