Synthetic studies on indoles and related compounds. 49. Unexpected formation of quinolone derivatives in Reissert indole synthesis was written by Suzuki, Hideharu;Gyoutoku, Hiroshi;Yokoo, Hiroe;Shinba, Mika;Sato, Yuka;Yamada, Hiroshi;Murakami, Yasuoki. And the article was included in Synlett in 2000.Quality Control of 3-Methyl-4-nitroanisole This article mentions the following:
The Reissert indole synthesis was found to unexpectedly give 3-hydroxy-1,2,3,4-tetrahydro-2-quinolone derivatives I (R = H, 6-MeO, 5-MeO, 3-CO2Et, 3-Me, 3-MeO, 3-Me2CHO), sometimes in a high ratio to the expected Et indole-2-carboxylate derivatives, depending on the conditions of the catalytic reduction of the intermediate (2-nitrophenyl)pyruvates. This reactivity is characteristic in the preparation of 7-substituted indoles. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitroanisole (cas: 5367-32-8Quality Control of 3-Methyl-4-nitroanisole).
3-Methyl-4-nitroanisole (cas: 5367-32-8) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly autoxidize to form hydroperoxides and dialkyl peroxides. If concentrated or heated, these peroxides may explode. To prevent such explosions, ethers should be obtained in small quantities, kept in tightly sealed containers, and used promptly.Quality Control of 3-Methyl-4-nitroanisole
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem