Potassium Carbonate → 1,2,3,4-Tetrahydro-6,7,8-trimethoxy-2-[2-(4-nitrophenyl)ethyl]isoquinoline

HRID 1451660

Reaktionsgleichung

Reaktionsgleichung von HRID 1451660
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[CH2:21][NH:20][CH2:19][CH2:18]2.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[CH2:21][N:20]([CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1)[CH2:19][CH2:18]2

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 792664-Nitrophenethyl bromideHCID 1927231,2,3,4-Tetrahydro-6,7,8-trimethoxyisoquinoline

Produkt 1

HCID 199745401,2,3,4-Tetrahydro-6,7,8-trimethoxy-2-[2-(4-nitrophenyl)ethyl]isoquinolineAusbeute 61,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 1-(2-bromoethyl)-4-nitrobenzene (0.34 g), 1,2,3,4-tetrahydro-6,7,8-trimethoxyisoquinoline [0.33 g; J. Chem. Soc. D, (20), 1296-1297 (1970)] and potassium carbonate (0.5 g) in DMF (20 ml) was heated at 50° for 12 h. The mixture was then filtered and the filtrate evaporated. The residue was taken up in water, extracted with dichloromethane, dried, evaporated and purified by column chromatography eluting with dichloromethane/methanol (99:1) to give the title compound (0.34 g) as a red solid, MP: 110°. NMR includes signals at d 3.55 (2H,s,N--CH2Ar), 3.70 (6H,s,OCH3), 3.75 (3H,s,OCH3).

Aufarbeitung

  1. temperaturewas heated at 50° for 12 h
  2. filtrationThe mixture was then filtered
  3. customthe filtrate evaporated
  4. extractionextracted with dichloromethane
  5. customdried
  6. customevaporated
  7. custompurified by column chromatography
  8. washeluting with dichloromethane/methanol (99:1)

Quellen und Nachweise

ORD-Eintrag
ord-e3a50547f5614d08b31602d8cef265af
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05604237

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