Synthesis of quinolines via ortho-lithiated N-acylanilines. A modified Friedlaender synthesis was written by Cho, In Seop;Gong, Leyi;Muchowski, Joseph M.. And the article was included in Journal of Organic Chemistry in 1991.Electric Literature of C12H17NO2 This article mentions the following:
A new variation of the Friedlaender quinoline synthesis was devised based on the sequential reaction of ortho-lithiated N–tert-Boc-anilines or N-pivaloylanilines with masked malondialdehyde derivatives, e.g., vinamidinium salts I (R = H, Ph), 3-(dimethylamino)acrolein, and 3-ethoxymethacrolein, and subsequent acid-induced cyclization. Thus, anilines II (R1 = H, F, Cl, Me, OMe, R2 = OCMe3) were lithiated and cyclized with I (R = H) to give quinolines III. Lithiation of II (R1 = F, R2 = CMe3) and cyclization with EtOCH:CMeCHO gave III (R1 = F, R = Me). In the experiment, the researchers used many compounds, for example, N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3Electric Literature of C12H17NO2).
N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. 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.Electric Literature of C12H17NO2
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem