M-Methoxyaniline

Problem 19.28 Prepare (a) 2-bromo-4-hydroxytoluene from toluene, (b) 2-hydroxy-5-methylbenzaIdehyde from p-toluidine, (c) m-methoxyaniline from benzenesulfonic acid. M... 

Beilstein Handbook Reference) AI3-52519 1-Amino-3-methoxybenzene 3-Aminoanisole m-Aminoanisole 3-Anisidine m-Anisidine m-Anisylamine Benzenamine, 3-methoxy- Benzenamine, 3-methoxy- BRN 0386119 CCRIS 5886 EINECS 208-6514 m-Methoxyaniline 3-Methoxyaniline 3-Methoxy-benzenamine NSC 7631. Chemical Intermediate. Liquid mp = -1° bp = 251° d = 1.0960 km = 285 nm (cyclohexane) slightly soluble in H2O, CCI4, soluble in EtOH, EtzO, MezCO, CeHe. Penta Mfg. Rhdne-Poulenc Sigma-Aldrich Fine Chem. 

Methoxyaniline. See p-Anisidine m-Methoxyaniline. See m-Anisidine o-Methoxyaniline. See o-Anisidine p-Methoxyaniline. See p-Anisidine... 

A solution of 2,3-dibromo-5-methoxyaniline (32 g, 0.17 mol) in CHjClj (300 ml) was stirred and cooled in an icc bath. Boron trichloride (1 M in CH2CI2, 180 ml, 0.18 mol), chloroacetonitrile (14.3 g, 0.19 mol) and TiC (1 M in CH CIj, 190ml, 0.19 mol) were added. The resulting mixture was refluxed for 1.5 h. The solution was cooled to room temperature and poured carefully on to a mixture of icc and 20% aq. HCl (700 ml). The organic layer was separated and the CH Clj removed by distillation. The residue was heated to 90°C on a water bath for 30 min. The solution was cooled and the solid collected by filtration. It was partitioned between ether (1.41) and 1 N NaOH (500 ml). The ether layer was washed with brine, dried over Na2S04 and evaporated. The residue was recrystallized from ethanol to give 2-amino-3,4-dibromo-6-methoxy-a-chloroacetophenone (55 g) in 90% yield. 

Chloro-2-methoxyaniline (2-amino-4-chloroanisole) [95-03-4] M 157.6, m 81-83°, 82-84°, 84°, 3.56. Purified by steam distn and recrystn from H2O or 40% aqueous EtOH. The N-acetate... 

General Conditions for each step and selectivity of m-substituted anilines As previously mentioned, Hauser and Reynolds reported on factors governing the first step of the Conrad-Limpach reaction but they tvere by no means exhaustive. Other than the conditions reported above for the first step, HClAleOH, CHCI3 or CHCI2 (neat or with acid catalyst), PhMe or PhH with removal of water with or without acid catalyst, or EtOH/AcOH/CaS04 were reported to provide the desired enamino-ester from an aryl amine and 3-keto-ester. Hauser and Reynolds also noted that o-nitroaniline and o-nitro-p-methoxyaniline failed to form the desired enamino-ester under conditions which they reported. 

Synonyms AI3-08584 2-Aminoanisole o-Aminoanisole l-Amino-2-methoxybenzene 2-Anis-idine 2-Anisylamine o-Anisylamine BRN 0386210 CCRIS 768 EINECS 201-963-1 2-Methoxy-l-aminobenzene 2-Methoxyaniline o-M ethoxy aniline 2-Methoxybenzenamine o-Methoxyphenylamine NSC 3122 UN 2431. 

Ammonium triselenimidate , see Ammonium 2,4,6-tris(dioxoselena) hexahydrotriazine-1,3,5-triide, 4586 Anilinium chloride, 2358 Anilinium nitrate, 2372 Anilinium perchlorate, 2360 Anisaldehyde, see 4-Methoxybenzaldehyde, 2951 m-Anisidine, see 3 -Methoxyaniline, 2813 o-Anisidine, see 2-Methoxyaniline, 2812... 

Figure 5.61 Schematic representation of a [Ru(bpy)3]2+/a-ZrP viologen structure on silica, plus the sequence of fast (1,2) and slow (3) electron transfer steps that follow photoexcitation of the photoactive ruthenium-containing polymer MDESA, p-methoxyaniline diethylsulfonate. Reprinted from Coord. Chem. Rev., 185-186, D. M. Kaschak, S. A. Johnson, C. C. Waraksa, J. Pogue and T. E. Mallouk, Artificial photosynthesis in lamellar assemblies of metal poly(pyridyl) complexes and metalloporphyrins, 403-416, Copyright (1999), with permission from Elsevier Science...

SYNS m-CRESIDINE 4-METHOXY-2-METHYL-ANILINE 4-METHOXY-2-METHYLBENZENAMINE 2-METHYL-4-METHOXYANILINE NCI-C02993... 

Condensation of aromatic nitroso compounds with primary amines is a satisfactory procedure for obtaining azo compounds. An example is the combination of nitrosobenzene and aniline in acetic acid, which results in a quantitative yield of azobenzene. Similarly, a series of methyl-substituted azobenzenes have been prepared, although the yields are poor in the case of the oriAo-substituted compounds. As an illustration of the versatility of the reaction, nitrosobenzene can be condensed with o-methoxyaniline (o-anisidine)," p-aminobenzoic acid, o-phenylene-diamine monobenzoate, and m-nitroaniline to form the corresponding substituted azobenzenes. 

Raposo, M., and Oliveira, Jr. O. N. Energies of adsorption of poly(o-methoxyaniline) layer-by-layer films. Langmuir 2000,16, pp. 2839-2844. 

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