1417652-57-3Relevant academic research and scientific papers
Preparation and x-ray crystal structure of 3-(4-(Dimethylamino)phenyl)-2- (phenylamino)isoquinolin-1(2H)-one, 3-(4-Methoxyphenyl)-2-(phenylamino) isoquinolin-1(2H)-one, and 2-Methyl-N′-(4-methylbenzoyl)-N′- phenylbenzohydrazide from Polylithiated 2-methylbenzoic Acid phenylhydrazide and methyl 4-dimethylaminobenzoate, methyl 4-methoxybenzoate, or methyl 4-methylbenzoate
Shuler, William G.,Smith, Ellyn A.,Hess, Sloan M.,McFadden, Thomas M. C.,Metz, Clyde R.,Vanderveer, Donald G.,Pennington, William T.,Mabe, Phillip J.,Knick, Shabree L.,Beam, Charles F.
, p. 952 - 959 (2012)
2-Methylbenzoic acid phenylhydrazide was polylithiated with excess lithium diisopropylamide, and the resulting polylithiated intermediate was condensed with methyl 4-dimethylaminobenzoate or methyl 4-methoxybenzoate to afford C-acylated intermediates that were immediately acid cyclized to afford 3-(4-(dimethylamino)-phenyl)-2-(phenylamino)isoquinolin-1(2H)-one C 23H21N3O or 3-(4-methoxyphenyl)-2-(phenylamino) isoquinolin-1(2H)-one C22H18N2O2. The polylithiated intermediate underwent N-acylation when it was condensed with methyl 4-methylbenzoate to give 2-methyl-N′-(4-methylbenzoyl)-N′- phenylbenzohydrazide C22H20N2O2. Crystals of C23H21N3O 4a are triclinic, P $ overline{1} $, a = 9.138(2) A, b = 10.519(2) A, c = 11.082(2) A, α = 91.55(3)°, β = 108.92(3)°, γ = 111.16(3)°, Z = 2, V = 927.1(3) A3, R 1 = 0.0711 and wR 2 = 0.1828 for reflections with I > 2σ(I); crystals of C22H18N2O2 4b are monoclinic, P21/c, a = 8.821(1) A, b = 13.276(2) A, c = 15.482(3) A, β = 105.271(4)°, Z = 4, V = 1748.9(5) A3, R 1 = 0.0416 and wR 2 = 0.1030 for reflections with I > 2σ(I); crystals of C22H20N2O2 3 are orthorhombic, Pbca, a = 13.505(3) A, b = 9.733(2) A, c = 28.601(6) A, Z = 8, V = 3759.4(13) A3, R 1 = 0.1683 and wR 2 = 0.3526 for reflections with I > 2σ(I). Index Abstract: X-ray crystal analysis was important for the confirmation of the structure of 3-(4-(dimethylamino)phenyl)-2-(phenylamino)isoquinolin-1(2H)-one C23H21N3O 4a, 3-(4-methoxyphenyl)-2- (phenylamino)isoquinolin-1(2H)-one C22H18N 2O2 4b, and 2-methyl-N′-(4-methylbenzoyl)-N′- phenylbenzohydrazide C22H20N2O2 3 prepared from polylithiated 2-methylbenzoicacid phenylhydrazide and methyl 4-dimethylaminobenzoate, methyl 4-methoxybenzoate, or methyl 4-methylbenzoate. Crystals of C23H21N3O 4a are triclinic, P, a = 9.138(2) A, b = 10.519(2) A, c = 11.082(2) A, α = 91.55(3)°, β = 108.92(3)°, γ = 111.16(3)°, Z = 2, V = 927.1(3) A3, R 1 = 0.0711 and wR 2 = 0.1828 for reflections with I > 2σ(I); crystals of C22H 18N2O2 4b are monoclinic, P21/c, a = 8.821(1) A, b = 13.276(2) A, c = 15.482(3) A, β = 105.271(4)°, Z = 4, V = 1748.9(5) A3, R 1 = 0.0416 and wR 2 = 0.1030 for reflections with I > 2σ(I); crystals of C22H20N2O2 3 are orthorhombic, Pbca, a = 13.505(3) A, b = 9.733(2) A, c = 28.601(6) A, Z = 8, V = 3759.4(13) A3, R 1 = 0.1683 and wR 2 = 0.3526 for reflections with I > 2σ(I).
