Polyazanaphthalenes. III. Some derivatives of 1,3,5-and 1,3,8-triazanaphthalene was written by Oakes, V.;Pascoe, R.;Rydon, H. N.. And the article was included in Journal of the Chemical Society in 1956.Recommanded Product: 50608-99-6 This article mentions the following:
Derivatives of 1,3,5- and 1,3,8-triazanaphthalenes were prepared from the corresponding 2,4-dihydroxy compounds 3-Aminopicolinic acid (I), m. 210°, (26 g.) was prepared by adding aqueous NaOBr, from 56 g. Br and 350 ml. 15% NaOH, to a solution of 50 g. quinolinimide in 1 l. of ice-cold 10% NaOH, and was kept at room temperature for 1 hr. and at 85° for 1 hr., cooled, adjusted to pH 5 with 50% H2SO4, filtered, added to Cu(OAc)2 and freed with H2S. Some 2-aminonicotinic acid (II) was obtained on filtration. The Et ester of I, m. 132°, and hydrazine hydrate gave 3-aminopicolinic hydrazide (III), m. 103°. III and acetone gave acetone 3-aminopicolinoylhydrazone, m. 172°, while NalO3 and in aqueous NH3 gave 3-aminopicolinamide, m. 184°; picrate, m. 214°. Similarly, the Et ester of II, m. 96°, 2-aminonicotinic hydrazide, m. 176° and acetone 2-aminonicotinoylhydrazone (IV), m. 179° were prepared IV and NaIO3 in aqueous NH3 gave 2-aminonicotinaldehyde. 2-R-4-R’ disubstituted 1,3,5-triazanaphthalene (IVa) (R = R’ = OH) (V) 6 g., m. above 380°, was prepared by heating a mixture of 13 g. I and 7 g. (H2N)2CO at 190-200° for 30 min., dissolving the product in 200 ml. 2N NaOH and precipitating with CO2. Distillation of V with Zn dust gave 1,3,4-triazaindene, m. 152°. 2,4-Dihydroxy-1,3,8-triazanaphthalene (VI), m. 361°, was prepared by the method of Robins and Hitchings (C.A. 50, 2604c). IVa (R = R’ == Cl) (VII) 3.25 g., m. 173°, was prepared by heating a mixture of 5 g. V, 75 ml. POCl3 and 10 ml. Et3N (VIII) for 6 hrs. VII was also obtained when PhNMe2 was used in place of VIII. Et2NH gave IVa (R = Cl, R’ = EtPhN), m. 168°. Reduction of VII over PtO2 or in the presence of MgO gave impure 1,3,5-triazanaphthalene, (picrate m. 191°). Other IVa were prepared by the reaction of VII with (H2N)2CS, EtSNa, and RONa were (R, R’-m.p. given): HS, HS (IX), 340°; EtS, EtS, 56°; MeO, MeO, 138°; EtO, EtO, 110°. A mixture of 3 g. Me2SO4, 250 mg. V, and 10 ml. 2N NaOH was shaken, allowed to stand overnight, NH4OH was added, the solution extracted with CHCl3 and on evaporation gave 140 mg. 1,2,3,4-tetrahydro-1,3-dimethyl-2,4-dioxo-1,3,5-triazanaphthalene, m. 246°. NH3 and 1 g. VII in 20 g. of boiling PhOH gave after cooling and treatment with 25% NaOH, IVa (R = R’ = NH2), m. 318°. Similarly in dioxane NH3 and VII gave IVa (R = Cl, R’ = NH2) (X), m. 265°. X and (H2N)2CS gave IVa (R = SH, R’ = NH2) (XI), m. 344°. IX and NH4OH gave XI. IVa (R = H, R’ = NH2) (XII), m. 224° was prepared by heating XI with Raney Ni in alc. NH3. IVa (R = H, R’ = HO) (XIII), m.p. 342° was prepared by heating 50 mg. XII with 8 ml. 5N HCl at 100° for 30 min. followed by treatment with 2N Na2CO3, and by heating I and HCONH2 at 130° for 2.5 hrs. and at 180° for 2.5 hrs. IVa (R = Cl, R’ = Et2N), m. 82°, and IVa [R = Cl, R’ = Et2N(CH2)3NH], m. 128° were prepared by heating the corresponding amine with VII in dioxane. N2H4.H2O and VII in cold dioxane gave on filtration 2 (or 4)-hydrazino-4(or 2)-hydroxy-1,3,5-triazanaphthalene, m. 385° and dilution of the dioxane filtrate with ethanol gave IVa (R = R’ = H2NNH), m. 266°. Similarly, the following derivatives of 2-R-4-R’ substituted 1,3,8-triazanaphthalene were prepared (R, R’, m.p. given). HO, HO, 361°; Cl, Cl, (XIV) 160°; EtS, EtS, 76°; NH2, NH2, 342°; Cl, NH2, above 360°; HS, HO, 360°; H, HO, 255-6°. Reduction of XIV over PtO2 or in the presence of MgO gave 5,6,7,8-tetrahydro-2,4-dimethoxy-1,3,8-triazanaphthalene. 3-Aminoisonicotinic acid formed a hydrazide, m. 187°. In the experiment, the researchers used many compounds, for example, 3-Aminopicolinamide (cas: 50608-99-6Recommanded Product: 50608-99-6).
3-Aminopicolinamide (cas: 50608-99-6) belongs to amides. Amides include many other important biological compounds, as well as many drugs like paracetamol, penicillin and LSD. Low-molecular-weight amides, such as dimethylformamide, are common solvents. Amides are stable compounds. The lower-melting members (such as acetamide) can be readily purified by fractional distillation. Most amides are solids which have low solubilities in water.Recommanded Product: 50608-99-6
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics