Methyl iodide → 1,2,3,4-Tetrahydro-1-methylquinoline

HRID 641918

Reaktionsgleichung

Reaktionsgleichung von HRID 641918
[H-].[Na+].[NH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1.I[CH3:14]>O1CCCC1>[CH3:14][N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 694601,2,3,4-Tetrahydroquinoline

Produkt 1

HCID 681091,2,3,4-Tetrahydro-1-methylquinolineAusbeute 64,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

NaH (12 g, 60%, 300.00 mmol) was added in several batches, to a solution of 1,2,3,4-tetrahydroquinoline (26.6 g, 199.70 mmol) in tetrahydrofuran (150 mL) at 0-5° C. The resulting solution was maintained at 0-5° C. for 30 minutes, then iodomethane (50 g, 352.11 mmol) was added dropwise (at 0-5° C.). The resulting solution was stirred at room temperature overnight. The mixture was filtered, and the filtrate was purified by column chromatography using a 1:100 ethyl acetate/petroleum ether solvent system to give 19 g (61%) of 1-methyl-1,2,3,4-tetrahydroquinoline as a yellow liquid.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. customthe filtrate was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-33b3645219aa43e4a460083cc587f271
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696229B2

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