Quinoline → Ethyl 3-aminopent-4-enoate

HRID 1108412

Reaktionsgleichung

Reaktionsgleichung von HRID 1108412
N1C2C(=CC=CC=2)C=CC=1.[H][H].[CH2:13]([O:15][C:16](=[O:22])[CH2:17][CH:18]([NH2:21])[C:19]#[CH:20])[CH3:14]>CCO.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[CH2:13]([O:15][C:16](=[O:22])[CH2:17][CH:18]([NH2:21])[CH:19]=[CH2:20])[CH3:14]

Komponenten

6

Edukt 3

HCID 7047QuinolineHCID 22006121Ethyl 3-amino-4-pentynoateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 10057602Ethyl 3-aminopent-4-enoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 16218511Pd barium sulfateKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 5% Pd/BaSO4 (0.025 g) and quinoline (0.30 mL) was stirred under a balloon of hydrogen for 30 minutes. 3-Amino-pent-4-ynoic acid ethyl ester (18-1) (for preparation, see J. A. Zablocki, et al., J. Med. Chem., 1995, 38, 2378-2394) (1.77 g, 10.0 mmol) in EtOH (15 mL) was added and the solution stirred for an additional 2.5 hours. The solution was filtered through a pad of celite and concentrated in vacuo to provide 2.65 g of crude product 18-2. 1H NMR (CDCl3, 300 MHz): δ 8.40-7.60 (br s, 2H), 6.11-5.96 (m, 1H), 5.58-5.53 (d, 1H), 5.44-5.41 (d, 1H), 4.31-4.16 (m, 3H), 3.12-2.86 (m, 2 H), 1.29-1.25 t, 3H). ##STR30##

Aufarbeitung

  1. filtrationThe solution was filtered through a pad of celite
  2. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c733a71549b54825bdcf63c9aaf280af
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06066648

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