Aniline, formation Butyl chloride

The earliest synthetic method for 1-benzazepine derivatives was a ring closure of -substituted anilines by C-N bond formation. Cyclization of 4-(2-aminophenyl butanoic acid and the corresponding butyl chloride gave the lactam (1, R1 = R2 = H) [1] and the 2-deoxo analogue [93], respectively. Thermal cyclization of (41, R1 = R2 = Me R3 = OH) gives 2,5-dioxo-benzazepines (38, R1 = R2 = Me R3 = R4 = R5 = H) [94]. Treatment of analogous esters with sodium hydride gives the derivatives of (38) [9, 95],... 

When the alcohol is readily available the reaction of an acid chloride and alcohol catalyzed hy base (pyridine, dimethyl-aniline, magnesium) is a standard mode of preparation of esters [4]. The procedure has been frequently employed in the formation of t-butyl esters [31, 32, 33, 34]. 

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