Eine neue Methode zur Reduktion eines Amids zum Amin mit der gleichen Anzahl von Kohlenstoffatomen

Abstract

An Hand von 9 Beispielen wird gezeigt, dass sich Säureamide im allgemeinen leicht mit Lithium‐Aluminium‐Hydrid zu den entspre‐chenden Aminen reduzieren lassen.

Hypolipidemic Activity of Phthalimide Derivatives V: Reduced and Hydrolytic Products of Simple Cyclic Imides

“…The second group includes vehicle-drug interactions. Of these, the capacity of the structure to dissolve (solubilize) the active substance, the related chemical potential difference of the drug in the vehicle and in the stratum corneum, and the diffusion rate of the drug through the vehicle are the most important (7). The vehicle is usually a liquid that is immobilized by the presence of polymers or solid particles (1).…”

Reduction of 2-chloro-N-phenylpropanamide and 2-methyl-N-phenylaziridine with lithium aluminium hydride

“…Melting points were measured on a Reichert melting point apparatus equipped with a microscope and are uncorrected. 1 H NMR (300 MHz) and 13 C NMR (75 MHz) spectra were recorded on a Varian instrument. Samples were dissolved in CDCl 3 purchased from Cambridge Isotope Labs.…”

“…The residue was subjected to column chromatography (SiO 2 , 5% MeOH in CH 2 Cl 2 ) to provide the product (5.3 g, 86%) as white solid. Mp 120-121 • C. 1 H NMR (300 MHz, CDCl 3 ): d = 1.57 (d, J = 7.5 Hz, 3 H), 2.21 (s, 3 H), 5.34 (q, J = 7.5 Hz, 1 H), 7.14 (t, J = 7.9 Hz, 1 H), 7.34 (t, J = 7.9 Hz, 2 H), 7.54 (d, J = 8.2 Hz, 2 H), 7.81 (s, 1 H). 13…”

“…Drying at oil pump provided the analytically pure product as white crystals in nearly quantitative yield. Mp 50-52 • C. 1 H NMR (300 MHz, CDCl 3 ): d = 1.53 (d, J = 6.9 Hz, 3 H), 2.55 (s, 1 H), 4.37 (q, J = 6.9 Hz, 1 H), 7.12 (t, J = 8.2 Hz, 1 H), 7.33 (t, J = 8.2 Hz, 2 H), 7.56 (d, J = 8.2 Hz, 2 H), 8.44 (s, 1 H). 13…”

“…Reduction of amides with lithium aluminium hydride (LiAlH 4 ) is a textbook reaction that yields the corresponding amine by reduction of the C=O group to CH 2 ; it was reported for the first time in 1948 by Uffer and Schlittler. 1 This reaction is normally straightforward for tertiary amides, but can be sluggish for secondary and in particular primary amides.…”