Methyl iodide → Methyl 1-methyl-1,2,3,4-tetrahydroquinoline-7-carboxylate

HRID 928425

Reaktionsgleichung

Reaktionsgleichung von HRID 928425
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[C:15]([O-])([O-])=O.[Cs+].[Cs+].IC>>[CH3:15][N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 3

HCID 6328Methyl iodide2×HCID 10796Cesium carbonateHCID 16244389Methyl 1,2,3,4-tetrahydroquinoline-7-carboxylate

Produkt 1

HCID 58081325Methyl 1-methyl-1,2,3,4-tetrahydroquinoline-7-carboxylate

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A suspension of methyl 1,2,3,4-tetrahydroquinoline-7-carboxylate (380 mg, 1.987 mmol), Cs2CO3 (1295 mg, 3.97 mmol) and iodomethane (0.118 ml, 1.888 mmol) was stirred for 16 hours at 20° C. After that time, more iodomethane (0.118 ml, 1.888 mmol) was added and stirring was continued for 8 hours at 60° C. The reaction mixture was allowed to cool to room temperature, filtered and concentrated under reduced pressure. The crude product was purified by preparative HPLC (Macherey-Nagel Nucleosil 100-10 C18, Flow 40 mL/min, ACN: 2 min at 5%, then to 100% within 17.5 min, RT 15.52 min) to yield the title compound. HPLC (Method H) Rt=3.005 min; MS (Method A) [M+H]+=206.1

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 8 hours at 60° C
  3. temperatureto cool to room temperature
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by preparative HPLC (Macherey-Nagel Nucleosil 100-10 C18, Flow 40 mL/min, ACN
  7. wait2 min at 5%, then to 100% within 17.5 min

Quellen und Nachweise

ORD-Eintrag
ord-cbca4275af2d4135bc96a25e4dfd630c
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290485B2

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