3-(4-Nitrobenzoyl)quinoline synthesis

6synthesis methods

Product Name:3-(4-Nitrobenzoyl)quinoline
CAS Number:1187166-16-0
Molecular formula:C16H10N2O3
Molecular Weight:278.26

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Yield:1187166-16-0 81%

Reaction Conditions:

with iron(III) chloride hexahydrate in 1,4-dioxane at 80; for 4 h;Michael addition-cyclization;

Steps:

A typical procedure for the FeCl₃·6H₂O catalyzed one-pot synthesis of 3-carbonyl quinolines from the reactions of ynones with 2-aminobenzaldehydes:

A solution of 1-phenylprop-2-yn-1-one (2a) (32.5 mg, 0.25 mmol) in 1,4-dioxane(2 ml) was added 2-aminobenzaldehyde (1a) (61 mg, 0.5 mmol) and FeCl₃·6H₂O (13.4 mg, 20 mol %), and the resulted reaction mixture was stirred at 80 ^oC for 4 h. After cooling to room temperature, the solvent was evaporated under vacuo and the residue was purified by chromatography on silica gel. A yellow solid of product (49 mg, 84%) 3awas obtained.

References:

Li, Hongfeng;Xu, Xiaolei;Yang, Jingyu;Xie, Xin;Huang, He;Li, Yanzhong [Tetrahedron Letters,2011,vol. 52,# 4,p. 530 - 533] Location in patent:supporting information; experimental part