Phenazine syntheses. VII. Certain disubstituted phenazines was written by Vivian, Donald L.. And the article was included in Journal of Organic Chemistry in 1956.Name: 1-Bromo-4-methoxybutane This article mentions the following:
Disubstituted phenazines are prepared by ring closure of substituted 2-nitrodiphenylamines. Refluxing 25 g. 2,6-(O2N)2C6H3Cl, 24 g. p-MeOC6H4NH2, 37.5 g. NaOAc.3H2O, and 375 cc. 95% EtOH 16 hrs. yields 91% 2,6-dinitro-4′-methoxydiphenylamine, small yellowish red needles, m. 171-3°, which (1 g.), heated 20 min. at 250-62° with (CO2)2Fe.2H2O (I) and 10 g. granulated Pb (II), gives 0.15 g. 7-methoxy-1-nitrophenazine, yellowish needles, m. 235-6°. Heating 76.5 g. N,N-dimethyl-p-phenylenediamine, 96 g. 2,5-(O2N)2C6H3Cl, and 90 g. anhydrous NaOAc 40 hrs. at 195-210°, steam distg, the mixture, adding 100 cc. HCl, steam distilling it again, and extracting the distillation residue with Et2O give 60 g. 4-chloro-4′-dimethylamino-2-nitrodiphenylmine, brick-red microcrystals, m. 144-6°, which (1 g.), heated with 1.3 g. I and 10 g. II 10-15 min. at 250-60°, yields 0.4 g. 2-chloro-8-dimethylaminophenazine, brownish red needles, m. 194-5°. Refluxing 20 g. 4,5-dinitroveratrole, 24.5 g. PhNH2, and 40 cc. absolute EtOH 3 weeks, steam distilling the mixture, and chromatographing the product on Al2O3 give 17.4 g. 4,5-dimethoxy-2-nitrodiphenylamine, orange needles, m. 120.5-1.5°, which (2 g.) heated 15 min. at 255-60° with 2.6 g. I and 20 g. II, yields 0.43 g. 2,3-dimethoxyphenazine, light yellow needles, m. 280-1°. Heating 28.1 g. 2,5-Br2C6H3NO2, 20.2 g. 5-bromo-2-anisidine, and 30 g. anhydrous NaOAc 40 hrs. at 200-10° yields 30.2 g. 4,5′-dibromo-2′-methoxy-2-nitrodiphenylamine, small red-orange needles, m. 198-200°, which (2 g.), heated 12 min. at 260° with 2.6 g. I and 20 g. II, yields 0.8 g. 2,7-dibromophenazine, bright yellow needles or prisms, m. 251-2°. Heating 200 g. 2,5-Cl2C6H3NO2, 200 g. o-MeC6H4NH2, and 200 g. NaOAc 40 hrs. at 180° gives 20.5% 4-chloro-2′-methyl-2-nitrodiphenylamine, orange prisms, m. 103-5°, which (10 g.), heated with 12 g. I and 100 g. II 12 min. at 270°, yields 3.5 g. 7-chloro-1-methylphenazine, yellow needles, m. 28-9°. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4Name: 1-Bromo-4-methoxybutane).
1-Bromo-4-methoxybutane (cas: 4457-67-4) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Name: 1-Bromo-4-methoxybutane
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary