Pyridine → 7-Iodo-2-methyl-4-pyrrolidin-1-yl-quinoline

HRID 1743905Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1743905
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([I:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.N1C=CC=CC=1>C(O)C.[I-].[K+]>[I:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)=[CH:3][C:4]([CH3:13])=[N:5]2)=[CH:10][CH:9]=1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 31268PyrrolidineHCID 220545164-Chloro-7-iodo-2-methylquinoline

Produkt 1

HCID 113366637-Iodo-2-methyl-4-pyrrolidin-1-yl-quinolineAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 4875Potassium IodideKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A suspension of 4-chloro-7-iodo-2-methylquinoline (EP497371, 2.00 g, 6.59 mmol) in ethanol (20 mL) was treated sucessively with pyrrolidine (1.28 g, 18.0 mmol), pyridine (0.2 mL) and potassium iodide (50 mg, 0.30 mmol), and the resulting mixture was refluxed for 24 h. After concentration in vacuo, the residue was taken up in water (50 mL) and basified to pH 12 by addition of 2 M aq. sodium hydroxide solution. The precipitate was collected by filtration, washed with water (20 mL) and ether (20 mL) and dried to afford the title compound (1.95 g, 87%). Off-white solid, m.p. 99–102° C.

Aufarbeitung

  1. temperaturethe resulting mixture was refluxed for 24 h
  2. concentrationAfter concentration in vacuo
  3. additionbasified to pH 12 by addition of 2 M aq. sodium hydroxide solution
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water (20 mL) and ether (20 mL)
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8e45da79a4894d0a8257605ab768506e
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07012073B2

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