Acetic Acid → 1-Ethyl-4-methyl-1,2,3,4-tetrahydroquinoline

HRID 279986

Reaktionsgleichung

Reaktionsgleichung von HRID 279986
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.C([BH3-])#N.[Na+].[OH-].[NH4+].[C:18](O)(=O)[CH3:19]>>[CH2:18]([N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:2]([CH3:1])[CH2:3][CH2:4]1)[CH3:19]

Komponenten

5

Edukt 4

HCID 176Acetic AcidHCID 102854-MethylquinolineHCID 14923Ammonium HydroxideHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 155556271-Ethyl-4-methyl-1,2,3,4-tetrahydroquinolineAusbeute 31 %

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

4-Methylquinoline (lepidine) (1.43 g, 10 mmol) and 50 ml of glacial acetic acid were added together and cooled to 10° C. Sodium cyanoborohydride (2.64 g, 42 mmol) was added gradually, and the reaction was stirred at 25° for 2 hours, and then heated at 55° for 11/2 hours. After stirring overnight at 25°, the reaction was neutralised with concentrated ammonium hydroxide to pH 10.5, and then the product was extracted into methylene chloride and evaporated. The crude product was purified on a silica gel column eluting with hexane to give 0.55 g (31% yield) of the title compound. MS: 175 (M+), 160 (M+ -Me); NMR: CDCl3 δ 1.22 (tr, J=7 Hz, 3, NCH2Me), 1.30 (d, J=3.5, 3, CHMe), 1.5-2.3 (m, 2, CH2), 2.89 (sextet, 1, CHMe), 3.29 (tr, 2, NCH2), 3.30 (quartet, 2, NCH2Me), 6.59 (m-tr, 2, Ar), 7.10 (m-tr, 2, Ar).

Aufarbeitung

  1. temperatureheated at 55° for 11/2 hours
  2. stirringAfter stirring overnight at 25°
  3. extractionthe product was extracted into methylene chloride
  4. customevaporated
  5. customThe crude product was purified on a silica gel column
  6. washeluting with hexane

Quellen und Nachweise

ORD-Eintrag
ord-da67f564164348cfbd7a4dbe8fb9be6f
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04587341

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