Beckmann rearrangements of 1-indanone oxime derivatives using aluminum chloride and mechanistic considerations was written by Lee, Byoung Se;Chu, Soyoung;Lee, In Young;Lee, Bon-Su;Song, Choong Eui;Chi, Dae Yoon. And the article was included in Bulletin of the Korean Chemical Society in 2000.Computed Properties of C9H8N2O3 This article mentions the following:
Hydrocarbostyril, which is a key intermediate in a new synthetic route to 6-nitroquipazine, can be prepared from 1-indanone oxime by Beckmann rearrangement. The reaction was optimized to 91% yield by using a Lewis acid, AlCl3, instead of common acids such as polyphosphoric acid, and H2SO4 used in conventional Beckmann rearrangement (20% in the literature, 10% in the authors’ experiment). The optimized condition was established with 3 equiv AlCl3 in CH2Cl2 at -40° to room temperature for 40 min. These conditions were applied to other 1-indanone derivatives, such as 4-methyl-, 4-methoxy- and 4- and 6-nitro-1-indanones. The mechanism of this reaction was proposed on the basis of the effect of temperature and substituent on product ratio, with the aid of PM3 calculation for a model system. In the experiment, the researchers used many compounds, for example, 7-Nitro-3,4-dihydroisoquinolin-1(2H)-one (cas: 22245-96-1Computed Properties of C9H8N2O3).
7-Nitro-3,4-dihydroisoquinolin-1(2H)-one (cas: 22245-96-1) belongs to isoquinoline derivatives. Although isoquinoline derivatives can be synthesized by several methods, relatively few direct methods deliver the unsubstituted isoquinoline. The Pomeranz–Fritsch reaction provides a method for the preparation of isoquinoline. This reaction uses a benzaldehyde and aminoacetoaldehyde diethyl acetal, which in an acid medium react to form isoquinoline.Computed Properties of C9H8N2O3
Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem