Isopropyl iodide → 2-(1-Methylethyl)-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline
Reaktionsgleichung
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[CH2:9][NH:8][CH2:7][CH2:6]2.I[CH:17]([CH3:19])[CH3:18].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:18][CH:17]([N:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][C:12]([N+:13]([O-:15])=[O:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:9]1)[CH3:19]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 65 °C
Versuchsvorschrift
6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline (222 mg, 1.07 mmol) was taken in acetonitrile (5 mL), treated with 2-iodopropane (0.8 mL, 5.0 mmol) and potassium carbonate (600 mg, 4.35 mmol, Aldrich). The mixture was heated at 65° C. for 16 h, cooled, and partitioned between ethyl acetate and water. The organic layer was separated, dried over magnesium sulfate, filtered, concentrated, and purified by chromatography on SiO2 (0 to 20% methanol/dichloromethane spiked with aqueous ammonia) to provide 2-(1-methylethyl)-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydro isoquinoline (0.24 g, 88%). 1H NMR (400 MHz, CDCl3) δ ppm 1.16 (d, J=6.4 Hz, 6 H), 2.76-2.84 (m, 2 H), 2.90-3.00 (m, 3 H), 3.70 (s, 2 H), 3.93 (s, 3 H), 6.80 (s, 1 H), 7.64 (s, 1 H); ESIMS (M+H)+=251.
Aufarbeitung
- temperaturecooled
- custompartitioned between ethyl acetate and water
- customThe organic layer was separated
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- custompurified by chromatography on SiO2 (0 to 20% methanol/dichloromethane spiked with aqueous ammonia)
Quellen und Nachweise
- ORD-Eintrag
- ord-16391d0078e64887a16058cc92a774e6
- Quelldatensatz
- uspto-grants-2011_07
- Patentnummer
- US07981903B2
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