Notes

Abstract

Some Pyndine and Quinaline Derivatives. By VLADIMIR A. PETROW. THE following miscellaneous experiments were carried out with the object of preparing naphthyridine derivatives. They were completed prior to the publication of Kermack and Weatherhead (J., 1942, 726).(a) 4-AndZinopyridine Dmioafives.--4.-Chlorop~cIine (25 g.) and aniline (21 g.) were heated under reflux on a wa'terbath. After 1 honse the crystalline product was dissolved in water, ammonia added in excess, the product collected, dried and extracted with hot benzene (700 d.). The insolnble fraction gave Cunilinopyridin+ hydmchhide (6-5 g.), flat needles from alcohol-ligroin, m. p. 227-228" (Found : C, 64-6; H, 5.4; N, 14.3; (2, 17.3. CllHIlN,C1 requires C, 64.0; H, 5-3; N, 13-6; C1, 17.3%). The benzene extract on concentration gave Panilinopyridine, m. p. 175-176O (22.5 g.) (Kermack and Weatherhead, Zoc. cit., give m. p. 173"). A solution of the base in conc. sulphuric acid gave an intense violet colouration with a trace of potassium nitrate and an immediate reddish-purple colouration with potassium dichromate. Neither the ucetyZ derivative, Iht plates from alcohol-lipin, m. p. 112-113" (Found: C, 73.6; H, 5-6; N, 13.1. CISHl*ON, requires C, 73-7; H, 6.7; N, 13*2%), nor the benzoyl derivative, prismatic needles from benzene-ligroin, m. p. 166-167" (Found: C, 78.8; H, Tl; N, l0.2-ClaH1dONa requires C, 789; H, 5.0; N, 10.4%), underwent cyclisation when heated with anhydrous Z I U C chlonde a t 300" for 3 hours. (b) N-(4'-Pyridyl)-anthraniZic Acid.-Anthradic acid (6.8 g.) in glacial acetic acid (20 ml.) was treated with khloropyridine (5.7 g.) under reflnx for 3 hours. When cold, the product was collected and crystallised from acetic acid containing a few drops of conc. hydrochloric acid. N-(4'-Pyridyl)-anthranilic acid hydrochloride formed stout needles. IIL p-282-283" (Found : C1, 14.2. Calc. for Cl&Xl,O,N,,HCl : Cl, 14.2%) (Kermack and Weatherhead, ZOC. cit., give m. p. 185"). The free atid, obtamed by treating the hydrochloride (1.0 g.) in dilute alcohol with crystalhe sodium acetate (800 mg.), formed needles fmm aq. alcohol, m. p. 283-284" (Found : C, 66.8; H, 4-7; N. 12.9. C&1oo&, requires C, 67-3 ; H, 4.7 ; N, 13.1%).Vigorons reaction occurred after ca. 15 minutes.Attempts to d e c t ring closure were unsuccessful.

Synthetic applications of N-N linked heterocycles. Part 15. A facile synthesis of 4-pyridyl(aryl)amines via the reaction between 4-chloro-1-pyridiniopyridinium salts and aryl amines

“…Chromatography of the crude products by t.1.c. showed the other fragment to be 2-cyanopyridine (13), n o trace of 4-cyanopyridine being detected. The same results were obtained using aqueous sodium cyanide, although in this case the product was more discoloured.…”

Crystal structure and DFT study of N-phenyl-N-(pyridin-4-yl)acetamide

“…The preparation of 1 was carried out according to the literature [2,3]. The single crystals were obtained by recrystallization from dichloromethane.…”

Crystal Structure and DFT Study of N-Phenyl-N-(Pyridin-4-Yl)acetamide

“…Experimental. The preparation of 1 was carried out according to the literature [ 2,3 ]. The single crystals were obtained by recrystallization from dichloromethane.…”

“…The single crystals were obtained by recrystallization from dichloromethane. X-ray data from a monoclinic crystal (colorless block, 0.10×0.05×0.05 mm) were collected on a RIGAKU Saturn 724+ CCD device at 93 K. Crystallographic parameters are as follows: space group P2 1 /n, a = 9.097(7) Å, b = 11.824(11) Å, c = 10.128(10) Å, β = 106.64 (2) -3 , F(000) = 448.00. The intensities of 7652 reflections (multi-layered mirror monochromatic MoK α radiation, 2θ max = 52°, R int = 0.0418 for 2027 unique reflections (1652 for I > 2σ(I )), numerical absorption correction) were measured; R(I > 2σ(I), all data) = 0.0425, 0.0567, wR(I > 2σ(I ), all data) = 0.0926, 0.0996, GOOF on F 2 = 1.050, Δρ max = 0.23 e/Å -3 , Δρ min = -0.23 e/Å -3 , Data / restrains / parameters = 2027 / 0 / 146.…”