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.Quality Control of tert-Butyl (4-chlorophenyl)carbamate 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, tert-Butyl (4-chlorophenyl)carbamate (cas: 18437-66-6Quality Control of tert-Butyl (4-chlorophenyl)carbamate).
tert-Butyl (4-chlorophenyl)carbamate (cas: 18437-66-6) belongs to organic chlorides. An organic chloride is an organic compound containing at least one covalently bonded atom of chlorine. Their wide structural variety and divergent chemical properties lead to a broad range of names and applications.While alkyl bromides and iodides are more reactive, alkyl chlorides tend to be less expensive and more readily available. Alkyl chlorides readily undergo attack by nucleophiles.Quality Control of tert-Butyl (4-chlorophenyl)carbamate
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics