Reaktion #51978

Reaktionsgleichung

Potassium hydroxide

H2O

acetonitrile

Trimethylsulfonium iodide

2-quinoline carboxaldehyde

→

title compound

2-(methylamino)-1-quinolin-2-ylethanol

Lösungsmittel

Et2O

Et2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to room temperature
2. 2
   Filtrationis filtered off
3. 3
   EinengenThe filtrate is concentrated in vacuo
4. 4
   Sonstigethe residue is re-subjected to the reaction conditions above and
5. 5
   Temperaturheated to 60° C. for 1 h
6. 6
   Temperaturto cool to room temperature
7. 7
   FiltrationThe precipitate is filtered off
8. 8
   Einengenthe filtrate is concentrated in vacuo
9. 9
   workup.DISSOLUTIONThe resulting crude epoxide (5.5 g) is dissolved in methanol (20 mL)
10. 10
    workup.ADDITIONadded to a 2.0 M solution of methylamine in methanol (100 mL)
11. 11
    TemperaturThe reaction mixture is heated
12. 12
    Temperaturto reflux for 1 h
13. 13
    Temperaturto cool to room temperature
14. 14
    Einengenconcentrated in vacuo
15. 15
    SonstigeThe resulting brown oil is purified via column chromatography (CHCl3/methanol, 95/5, 90/10; CHCl3/methanol/NH4OH, 90/10/1)

Vorschrift

Potassium hydroxide (3.21 g) and H2O (0.13 mL) are added to acetonitrile (50 mL). Trimethylsulfonium iodide (5.84 g) and 2-quinoline carboxaldehyde (4.50 g) are then added. The reaction mixture is heated to 60° C. for 4 h. The reaction mixture is allowed to cool to room temperature and is diluted with Et2O (25 mL) The precipitate is filtered off. 1H NMR of an aliquot of the filtrate showed mostly starting material and a small amount of the desired epoxide. The filtrate is concentrated in vacuo and the residue is re-subjected to the reaction conditions above and heated to 60° C. for 1 h. The reaction mixture is allowed to cool to room temperature and is diluted with Et2O (25 mL). The precipitate is filtered off and the filtrate is concentrated in vacuo. The resulting crude epoxide (5.5 g) is dissolved in methanol (20 mL) and added to a 2.0 M solution of methylamine in methanol (100 mL). The reaction mixture is heated to reflux for 1 h. The reaction mixture is allowed to cool to room temperature and concentrated in vacuo. The resulting brown oil is purified via column chromatography (CHCl3/methanol, 95/5, 90/10; CHCl3/methanol/NH4OH, 90/10/1) to yield 1.191 g of the title compound as a yellow-green oil.

Quelle