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Crystal structure of N -(2-benzoyl-5-ethynylphen ­ yl)quinoline-2-carboxamide

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ABSTRACT

In the title compound, C25H16N2O2, the quinoline ring system is essentially planar, with a maximum deviation of 0.030 (1) Å, and forms a dihedral angle of 20.9 (1)° with benzoyl benzene ring. The unsubstituted phenyl ring forms dihedral angles of 52.7 (1)° with the quinoline ring system and 54.1 (1)° with the ethynyl-substituted benzene ring. The mol­ecule contains an intra­molecular bifurcated N—H⋯(O,N) hydrogen bond, forming S(5) and S(6) rings, which may influence the conformation of the mol­ecule. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional network. In addition, the three-dimensional structure contains π–π stacking inter­actions, with centroid–centroid distances of 3.695 (1) and 3.751 (1) Å.

No MeSH data available.


The reaction scheme for the synthesis of the title compound.
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fig3: The reaction scheme for the synthesis of the title compound.

Mentions: The title compound was prepared using 3-bromo­aniline (1, Fig. 3 ▸) as starting reagent in the presence of boron trichloride (1.1 equiv), AlCl3 (1.1 equiv) and benzo­nitrile (3 equiv) for 24 h at approximately 353 K. The solution was extracted with DCM, dried and concentrated to obtain (2-amino-4-bromo­phen­yl)(phen­yl)methanone (2) (petroleum ether:ethyl acetate 9:1, 0.52). Compound 2 (1.8 mmol) was dissolved in tri­ethyl­amine, Pd(PPh3)2Cl2 (0.05 eq), tri­methyl­silyl­acetyl­ene (1.5 eq) and copper iodine (0.1 eq) were added and the solution was heated to approximately 343 K overnight. The organic phase was separated and concentrated (petroleum ether:ethyl acetate 7:1, 0.70) and the fraction containing the product (75%) was collected and used for the next step. A solution of compound 3 (0.4 mol, 1 eq) in tetra­hydro­furane was stirred and cooled in an ice bath, tetra-n-butyl­ammonium fluoride (1.5 eq) was added and the reaction was stirred for two hours. The organic layer was separated and dried over magnesium sulfate to obtain compound 4 (petroleum ether:ethyl acetate 7:1, 0.60). The title compound (I) (Fig. 3 ▸) was prepared by refluxing a mixture of quinaldic acid, tri­ethyl­amine, p-toluene­sulfonyl chloride and compound 4 for 24 h in di­chloro­methane. After evaporation of the CH2Cl2, the compound was purified by silica column chromatography (petroleum ether:ethyl acetate 7:1, 0.36). Single colourless block-shaped crystals of (I) were obtained by slow evaporation in di­chloro­methane in a closed flask with petroleum ether.


Crystal structure of N -(2-benzoyl-5-ethynylphen ­ yl)quinoline-2-carboxamide
The reaction scheme for the synthesis of the title compound.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5382631&req=5

fig3: The reaction scheme for the synthesis of the title compound.
Mentions: The title compound was prepared using 3-bromo­aniline (1, Fig. 3 ▸) as starting reagent in the presence of boron trichloride (1.1 equiv), AlCl3 (1.1 equiv) and benzo­nitrile (3 equiv) for 24 h at approximately 353 K. The solution was extracted with DCM, dried and concentrated to obtain (2-amino-4-bromo­phen­yl)(phen­yl)methanone (2) (petroleum ether:ethyl acetate 9:1, 0.52). Compound 2 (1.8 mmol) was dissolved in tri­ethyl­amine, Pd(PPh3)2Cl2 (0.05 eq), tri­methyl­silyl­acetyl­ene (1.5 eq) and copper iodine (0.1 eq) were added and the solution was heated to approximately 343 K overnight. The organic phase was separated and concentrated (petroleum ether:ethyl acetate 7:1, 0.70) and the fraction containing the product (75%) was collected and used for the next step. A solution of compound 3 (0.4 mol, 1 eq) in tetra­hydro­furane was stirred and cooled in an ice bath, tetra-n-butyl­ammonium fluoride (1.5 eq) was added and the reaction was stirred for two hours. The organic layer was separated and dried over magnesium sulfate to obtain compound 4 (petroleum ether:ethyl acetate 7:1, 0.60). The title compound (I) (Fig. 3 ▸) was prepared by refluxing a mixture of quinaldic acid, tri­ethyl­amine, p-toluene­sulfonyl chloride and compound 4 for 24 h in di­chloro­methane. After evaporation of the CH2Cl2, the compound was purified by silica column chromatography (petroleum ether:ethyl acetate 7:1, 0.36). Single colourless block-shaped crystals of (I) were obtained by slow evaporation in di­chloro­methane in a closed flask with petroleum ether.

View Article: PubMed Central - HTML - PubMed

ABSTRACT

In the title compound, C25H16N2O2, the quinoline ring system is essentially planar, with a maximum deviation of 0.030 (1) Å, and forms a dihedral angle of 20.9 (1)° with benzoyl benzene ring. The unsubstituted phenyl ring forms dihedral angles of 52.7 (1)° with the quinoline ring system and 54.1 (1)° with the ethynyl-substituted benzene ring. The mol­ecule contains an intra­molecular bifurcated N—H⋯(O,N) hydrogen bond, forming S(5) and S(6) rings, which may influence the conformation of the mol­ecule. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional network. In addition, the three-dimensional structure contains π–π stacking inter­actions, with centroid–centroid distances of 3.695 (1) and 3.751 (1) Å.

No MeSH data available.