Pyridine → 2-(4'-Benzamidophenyl)butyric acid

HRID 249545

Reaktionsgleichung

Reaktionsgleichung von HRID 249545
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([CH2:21][CH3:22])[C:18]([OH:20])=[O:19])=[CH:13][CH:12]=1.N1C=CC=CC=1.CCOCC>C1COCC1>[C:1]([NH:10][C:11]1[CH:12]=[CH:13][C:14]([CH:17]([CH2:21][CH3:22])[C:18]([OH:20])=[O:19])=[CH:15][CH:16]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 7412Benzoyl chlorideHCID 346552-(4-Aminophenyl)butanoic acid

Produkt 1

HCID 229189622-(4'-Benzamidophenyl)butyric acidAusbeute 47,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Benzoylchloride (7.84 g, 0.057 mol) was added dropwise to a solution of 2-(4'-aminophenyl)butyric acid (10.0 g, 0.057 mol) and pyridine (4.85 g, 0.061 mol) in 100 mL of THF at 0° C. After 30 minutes the ice bath was removed and the reaction warmed to room temperature. After 1 hour the suspension was diluted with 300 mL of ether, washed with 10% HCl (3×50 mL), saturated NaCl (50 mL), dried over MgSO4 and evaporated to give a brown solid. Trituration with ether afforded 7.54 g (47.7%) of the product as a white solid.

Aufarbeitung

  1. customAfter 30 minutes the ice bath was removed
  2. additionAfter 1 hour the suspension was diluted with 300 mL of ether
  3. washwashed with 10% HCl (3×50 mL), saturated NaCl (50 mL)
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customto give a brown solid

Quellen und Nachweise

ORD-Eintrag
ord-a9a0ca91bae14a2d9d5189005baba691
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05214191

Verknüpfte Notizen

Wird geladen…