Aniline methoxy

The Gassman indole synthesis has one serious limitation. Attempts to use anilines with an ortho/para- methoxy moiety failed to indolize. One means to overcome this was synthesis of the corresponding oxindoles followed by reduction to the indoles. ... 

The yield of 3//-azepine appears to be influenced by substituents on the azide ring although no in-depth study has been reported. 4-Halophenyl azides, in most cases, give rise to complex mixtures of products.177 4-Tolyl azide, on thermolysis in aniline, yields 5-methyl-iV-phenyl-3//-azepin-2-amine (18% mp 157-158°C), whereas the thermolyses of 4-methoxy-, 4-methyl-, 4-chloro-, and 4-nitrophenyl azides in a range of arylamines (4-chloro-, 4-methoxy-, and pen-tafluoroaniline) yield only azo compounds and uncharacterized tarry products.178... 

Likewise, thermolysis of 4-azidophenyl methyl ketone in methanol yields 5-acetyl-2-methoxy-3//-azepine (60%), compared to only an 8% yield from the photolytic reaction.78 119 The thermolysis of phenyl azide in refluxing cyclohexanol yields no 3H-azepine, only diphenyl-diazene (10%) and aniline (30%).74 In contrast, thermolysis of methyl 2-azidobenzoate in cyclohexanol furnishes a mixture of methyl 2-(cyclohexyloxy)-3//-azepine-3-carboxylate (20 % bp 127°C/0.1 Torr) and methyl 2-aminobenzoate (60%). Thermolysis of the azido ester in methanol under nitrogen in an autoclave at 150 C yields a 7 10 mixture (by 1HNMR spectroscopy) of the amino ester and methyl 2-methoxy-3//-azepine-3-carboxylate, which proved to be difficult to separate, and much tar.74 The acidic medium179 is probably responsible for the failure of methyl 2-azidoberjzoate to yield a 3//-azepine when thermolyzed in 3-methoxyphenol aniline (40%) is the major product.74... 

A -Phenyl-3//-azepin-2-amine (3), obtained in 25% yield by heating 2-methoxy-3//-azepine with aniline at 120 C for four hours,81 in refluxing ethanolic sodium benzenethiolate undergoes displacement of aniline and forms 2-(phenylsulfanyl)-3//-azepine (4).116... 

Amyl bromide [Pentane, 1-bromo-], 82 Aniline [Benzenamine], 122 Anilines, o-alkylation of, 15 Anisole [Benzene, methoxy-], 48 Amsyl chloride [Benzene, l-(chloromethyl)-... 

Aniline, 2-chloro- [Benzenamine 2-chloro-], p-bromination of, 55, 23 Aniline, 3 chloro- [Benzenamine, 3-chloro-], p bjomination of, 55, 23 Aniline, //.A -diethyl- [Benzenamine, N,N-diethyl-], p-bromination of, 55, 23 Aniline,TV,//-dimethyl- [Benzenamine, N,N-dimethyl-], p-brommation of, 55, 23 Aniline, 2,3-dimethyl- [Benzenamine, 2,3-dimethyl-], p-bromination of, 55, 23 Aniline, 2,5-dimethyl- [Benzenamine, 2,5-dimethyl-], p-biomination of, 55,23 Aniline, 3,5-dimethyl [Benzenamine, 3,5-dimethyl ], p bromination of, 55,23 Aniline, Ar,iV-dimethyl-3-(trifluoromethyl) [Benzenamine, At,Ar-dimethyl-3-tn-fluoromethyl-], 55,21 Aniline, 3-methoxy- [Benzenamine, 3-methoxy-], p-bromination of, 55, 23 Aniline, TV-methyl- [Benzenamine, //-methyl-], p-biomination of, 55, 23 Aniline, 2-methyl-//,JV-dimethyl- [Benzen-amme, 2/V,/V-tnmethyl-], p-bromina-tion of, 55, 23... 

Methoxy-anilin 4-MethyI-anilin 4-Brom-anilin 3-Nitro-anilin I-Naphthylamin... 

Chlor-anilin 4-Methoxy-unilin 4-Amino-benzvesaure-methy /ester 4-Amino-benzonitril... 

In geteilter Zelle und 2 n Schwefelsaure laBt sich Phenol an Platin-Kathoden zu Cyclo-hexanol hydrieren (niedrige Stromdichte 56% d.Th.)6,7. Analog reagieren Methyl-phe-nole, -aniline und -benzoesauren sowie Methoxy-toluole usw.7. 1-Naphthol wird zu 7-Hydroxy-dekalin und 2-Naphthol zu 6-Hydroxy-tetralin in mittleren Ausbeuten reduziert7. 

The somewhat analogous substrate, p-methoxy-A-(2-nitroprop-l-enyl)aniline (15), afforded 6-methoxy-3-methylquinoxaline 4-oxide (16) (98% H2SO4 %). ... 

After a few minutes 2,4-diamino-6-methylphenol (hRf 5-10), 3-chloro-4-methoxy-aniline (hJ f 25-30), aniline (hRf 35-40), 4-bromoaniline (hRf 40-45), 3-chloroaniline (hJ f 50-55), 2,6-dimethylaniline (hi f 60-65), 2-methyl-6-ethylaniline (hi f 65-70) and 2-chloroaniline (hRj 70-75) yielded orange-colored chromatogram zones on a yellow background. The detection limits were between 5 ng (2,4-diamino-6-methylphenol) and 30 ng (2,6-dimethylaniline) substance per chromatogram zone. 

El-Fantroussi S (2000) Enrichment and molecular characterization of bacterial culture that degrades methoxy-methyl urea herbicides and their aniline derivatives. Appl Environ Microbiol 66 5110-5115. 

Various mixed tridentate ligands with P,N,0/S/N donor sets have been explored in Ni11 chemistry. For example, condensation of 2-(diphenylphosphino)aniline with substituted (5-chloro-, 5-nitro, 5-bromo-, 5-methoxy-, and 3-methoxy-) salicylaldehydes yields (253).697 The deprotonated ligand coordinates through its P,N,0 donor set in a square planar geometry with some distortion, which is probably due to the bulk of the phosphine group and to the bite angle of the P,N chelate. 

To get a complex set of substituents by direct derivatization of benzotriazole is not feasible. In such situations, it is better to have all the substituents in place first and later construct the heterocyclic ring. High reactivity of anilines and their well-developed chemistry makes them good stating materials. In an example shown in Scheme 215, acetanilide 1288 is nitrated to afford nitro derivative 1289 in 73% yield. Catalytic reduction of the nitro group provides methyl 4-acetylamino-3-amino-5-chloro-2-methoxybenzoate 1290 in 96% yield. Nitrosation of compound 1290 in diluted sulfuric acid leads to intermediate 1291, which without separation is heated to be converted to 7-chloro-4-methoxy-l//-benzotriazole-5-carboxylic acid 1292, isolated in 64% yield <2002CPB941>. 

As is also illustrated in Scheme 6.23, the optically enriched amino nitriles can be converted to the corresponding a-amino esters through a four-step sequence (74—> 75). Unlike the aforementioned imine alkylations with alkylzinc reagents, methylation of the phenolic OH is required, since the corresponding o-methoxy aniline is less reactive and affords significantly lower enantioselectivities similar observations are made when aniline is used. 

If 3-methoxy-aniline is used, 6-methoxy-DET will probably result, but if 3,5-dimethoxyaniline is used, 4,6-dimethoxy-DET should be obtained. 

A 1M p-methoxy-aniline (p-anisidine), 0.5 M ethyl-gamma-Br-acetoacetate (brominate as described above for 1-methyl-DET synthesis) cool and add 250 ml ether. Filter, evaporate in vacuum and reflux residue fifteen hours with 60 g ZnCI2 in 250 ml ethanol. Evaporate in vacuum, wash precipitate with water and dissolve residue in benzene. Wash with 4N HCI and water and dry, evaporate in vacuum. Reflux prcipitate two hours in ethanol-KOH to get about 70% yield of 5-methoxy-indoleacetic acid (I). 

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