Arthur, H. R.; Ng, Y. L. published an article in 1959, the title of the article was Examination of the rutaceae of Hong Kong. IV. Synthesis of dihydronitidine.Category: amides-buliding-blocks And the article contains the following content:
Dihydronitidine (I) was synthesized and the structures for nitidine (II) and oxynitidine (III) proposed in the earlier work confirmed. Acetopiperone (25 g.) and 30 g. veratraldehyde treated with 150 ml. alc. with 30 ml. 10% aqueous NaOH gave 30 g. 3,4-dimethoxy-3′,4′-methylenedioxychalcone (IV), m. 135° (alc.). IV (30 g.) in 110 ml. EtOCH2CH2OH containing 6.5 ml. AcOH treated 3 min. at 100° with 12.5 g. KCN in 45 ml. H2O, heating continued 10 min., 150 ml. H2O added, and the mixture cooled gave 30 g. α-(3,4-dimethoxyphenyl)-γ-(3,4-methylenedioxyphenyl)-α-oxobutyronitrile (V), yellow needles, m. 146° (alc.). V (30 g.) in 200 ml. AcOH treated gradually with 30 ml. concentrated H2SO4 gave 25 g. α-(3,4-dimethoxyphenyl)-γ-(3,4-methylenedioxyphenyl)-γ-oxobutyramide (VI), m. 177° (alc.). VI (25 g.) in 350 ml. 7% aqueous NaOH and 200 ml. alc. refluxed 10 hrs. and then acidified gave 22 g. α-(3,4-dimethoxyphenyl)-γ-(3,4-methylenedioxyphenyl)-γ-oxobutyric acid (VII), needles, m. 172° (alc.). VII (11 g.) in 110 ml. AcOH containing 2 ml. 70% HClO4 hydrogenated during 2 hrs. at 60°/1 atm. over 2 g. 5% Pd-C, most of the solvent removed, H2O added, the oily product extracted with C6H6, the 8 g. brown oil [α-(3,4-dimethoxyphenyl)-γ-(3,4-methylenedioxyphenyl)-butyric acid] refluxed 4 min. with 20 ml. POCl3, the mixture poured on ice, the solid dissolved in CHCl3, washed with aqueous NaOH, H2O, dried, and evaporated gave 6.5 g. 2-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydro-6,7-methylenedioxy-1-oxonaphthalene (VIII), m. 165° (alc.). VIII(6 g.) in 15 ml. HCONH2 and 0.8 ml. HCO2H heated 3 hrs. at 180° with 0.8 g. (NH4)2SO4, 0.8 ml. HCO2H added hourly, the mixture cooled, diluted with H2O, extracted with CHCl3, washed, and evaporated gave 3.5 g. 2-(3,4-dimethoxyphenyl)-1-formamido-1,2,3,4-tetrahydro-6,7-methylenedioxynaphthalene (IX), m. 178° (dioxane-alc.). IX (1.5 g.) refluxed 15 min. with 3 ml. POCl3 in 10 ml. PhMe gave a solid which suspended in MeOH and basified gave 1 g. 3,4,11,12-tetrahydro-6,7-di-methoxy-2′,3′-methylenedioxy-1,2-benzophenanthridine (X), m. 188-9° (MeOH). X (0.9 g.) heated 0.5 hr. at 240° with 0.2 g. 30% Pd-C and extracted with CHCl3 gave 0.6 g. 6,7-dimethoxy-2′,3′-methylenedioxy-1,2-benzophenanthridine (XI), m. 273° (C5H5N). XI (0.5 g.) in 5 ml. xylene and 10 ml. PhNO2 refluxed a few min. with 1 ml. Me2SO4 gave the methosulfate of XI, m. 306-7° (decomposition) (aqueous alc.). XI methosulfate (0.4 g.) in 60 ml. H2O and 4 ml. concentrated HCl refluxed 5 hrs. with 8 g. Zn powder under argon, 3 ml. more HCl added after each hr., the solution cooled to 0-5°, sealed 12 hrs. under argon, the solid washed, shaken with CHCl3 and NH3, the extract washed, dried, and evaporated gave 0.2 g. I, prisms, m. 208-11° (alc.). Simple transformations used for I led to syntheses of II and III. The experimental process involved the reaction of N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide(cas: 456-12-2).Category: amides-buliding-blocks
N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide(cas:456-12-2) belongs to amides. Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis. Category: amides-buliding-blocks
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics