Pyrrolidine → HCID 23022384, Verbindung

HRID 351346Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 351346
[NH2:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([CH:6]=[C:7]([CH:13]=O)[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.C(=O)([O-])O.[Na+]>ClC(Cl)C>[CH3:12][C:11]1[C:2]([NH2:1])=[CH:3][CH:4]=[C:5]2[C:10]=1[N:9]=[CH:8][C:7]([CH2:13][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)=[CH:6]2

Komponenten

5

Edukt 3

HCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 230223367-Amino-8-methylquinoline-3-carbaldehyde

Produkt 1

HCID 23022384HCID 23022384, VerbindungAusbeute 94,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

To a suspension of 7-amino-8-methyl-3-quinolinecarboaldehyde (21.00 g, 112.8 mmol) obtained in Reference Example 66 in dichloroethane (210 ml) were added pyrrolidine (28.28 ml, 145.0 mmol) and triacetoxy sodium borohydride (35.84 g, 169.2 mmol), and the mixture was stirred at room temperature for 4.5 hrs. To the reaction solution was added saturated aqueous sodium hydrogen carbonate and the mixture was vigorously stirred. The organic layer was separated and concentrated under reduced pressure. The residue was purified by NH-silica gel column (Fuji Silysia Chemical Lyd., Pro. No. DM1020, eluting solvent: ethyl acetate) to give the title compound (25.7 g) as a viscous oil.

Aufarbeitung

  1. stirringthe mixture was vigorously stirred
  2. customThe organic layer was separated
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by NH-silica gel column (Fuji Silysia Chemical Lyd
  5. washDM1020, eluting solvent

Quellen und Nachweise

ORD-Eintrag
ord-b025d315912149dbabd12f93e307ebcf
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183415B2

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