Acetic acid aminophenyl

A rhodium-on-alumina catalyst deactivated in bis-(4-aminophenyl)-methane saturation (I IS C, 100 psig) was regenerated by two washings with aqueous ammonia at 65°C, followed by drying at 90°C(I6) or by washing with acetic acid. 

D(-)-0i-(Aminophenylacetamido)l penicillanic acid (Ampicillin) Metampicillin sodium Piperacillin sodium a-Aminophenyl acetic acid Ampicillin... 

N-(4-Fluoro-3-aminophenyl)aminomethylenemalonate (1586) was reacted with dimethoxytetrahydrofuran in boiling glacial acetic acid for 3-4 min to give /V-[4-fluoro-3-(l-pyrrolyl)phenyl]aminomethylenema-lonate (1587) in 87% yield (86FRP2574404). 

The 1,2,3-triazine ring was constructed from o-aminophenyl oximes in the conditions of nitrosation (NaN02/HCl) , while hydrazinooximes were used for the synthesis of the 1,2,4-triazine ring Thus, cyclization of a-hydrazinooxime 342 with Pb304 in the presence of acetic acid afforded 1,2,4-triazines 343 in 44-54% yields (equation 149) . Interaction of oxime 344 with hydrazine leads to the spiro compound product 345 in 73% yield (equation 150) °. 

Schonberg et al. reportedly obtained the photodimer in excellent yields when a solution of 138 in diethyl phthalate was heated to 270°C for 30 minutes and then rapidly chilled with ice water (on slow cooling no dimer was obtained see also Mustafa ). These observations could not be substantiated a product obtained in this way (mp 200°C) differed from the photodimer (comparison of IR spectra). The structure of this product is not known. A dimer was also obtained when 1,3-bis(dimethyl-aminophenyl)benzo[c]furan was treated with acetic acid with sulfuric acid it was reconverted to the monomer. . There seem to be no reports concerning the photodimerization of other benzo[cjfurans. As we have found,... 

The benzene ring has been proposed as an isosteric replacement in a dipeptide to enforce either the tram l1 1 or the cis conformation 312>31 (Scheme 1). Similarly, 2-(amino-methyl)pyrrole-l-acetic acid (8, R = H) has been proposed as a cis peptide bond mimic,141 having the same number of atoms between the amino and carboxylic acid functions as in a dipeptide. Several other amino- and carboxy-substituted aromatic structures have been used as spacers in peptides 2-, 3-, and 4-aminobenzoic acids (Abz, e.g., 7), 2-, 3-, and 4-(amino-methyl)benzoic acids (Amb, e.g., 2), 2-, 3-, and 4-(aminophenyl)acetic acids (APha, e.g., 5), 2- (4), 3-, and 4-(aminomethylphenyl)acetic acid (Ampa), (aminomethyl)pyrrole-, -thiophene-, and -furancarboxylic acids 6, (aminomethyl)pyrrole- 8 and -thienylacetic acids, and aminobiphenylcarboxylic acids. 

An intimate mixture consisting of 1 molecular equivalent of the zinc salt of o-aminophenyl selenide and 2 equivalents of p-nitrobenzoyl chloride is fused for an hour at 100° C. The cooled melt is then pulverised and washed successively with water and sodium carbonate solution. Repeated crystallisation from glacial acetic acid gives pale yellow lustrous needles, M.pt. 211c C. (corr.). 

Aryl-5,6-dihydrobenzo[4,5]imidazo[l,2-C]-quinazolines Isatoic anhydride could also be reacted with amino-, hydroxyl- or thiolanilines to form 2-(2-aminophenyl)benz-imidazoles, oxazoles or thiazoles, Scheme 5.38. In the case of 2-(2-aminophenyl)benzimidazoles (X=N), the product was formed after 3 min at 150°C in acetic acid. The products could subsequently be further elaborated 6-aryl-5,6-dihydrobenzo[4,5]imidazo[l,2-C]quinazolines, a four ring system, was formed by treatment of the 2-(2-aminophenyl) benzimidazole (X=N) with different aldehydes in acetic acid at 150°C for 5 min (J. Westman, and K. Orrling, Personal Chemistry, Uppsala, Sweden, unpublished results). Fifteen compounds were synthesised in 20-75% overall yield. This 3 + 5 min procedure should be compared to the conventional heating protocol developed by Devi and co-workers57, where each reaction step was run overnight to eventually afford the products in only 30-50% yield. 

Yoda,104 after reacting non-reducing sugars and polyhydric alcohols with periodate, used a mixture of manganous sulfate and bis-(p-dimethyl-aminophenyl)methane in acetic acid to detect the spots sensitivity, 5 to 50 micrograms. 

Reaction of (2-aminophenyl)-(4-bromophenyl)-methanone with methylsulfanylacetic acid ethyl ester and tert-butyl hypochlorite gives a corresponding sulfonium salt. This salt was transformed to initially to the betaine. Electrocyclic rearrangement of that transient intermediate leads, after rearomatization, to the homoanthranilic acid. Internal ester-amine interchange leads then to 4-bromophenyl-(3-(methylthio)indolin-7-yl)methanone. The thiomethyl group is then removed with Raney nickel to give 4-bromophenyl-(indolin-7-yl)methanone. Saponification of this intermediate affords the (2-amino-3-(4-bromobenzoyl)-phenyl)-acetic acid (Bromfenac). 

The solution of N-acetyl-N-(3-aminophenyl)-p-amino-isobutyric acid was filtered after standing overnight, mixed with an equal volume of acetic acid, and there after with a solution of 275.0 g iodine monochloride and 200.0 g sodium chloride in 1 L water. The mixture was kept at 50°C with stirring for 48 h. Light brown crystals of crude N-acetyl-N-(2,4,6-triiodo-3-aminophenyl)-p-amino-isobutyric acid precipitated, were filtered off, washed with water, and dried. They weighed 195.0 g (84.5% yield based on N-acetyl-N 3-nitrophenyl-p-amino-isobutyric acid). 

Amino-4-nitrophenol, 25, 5 2-Amino-5-nitrotoluene, 20, 73 22, 44 (7/-ar-AMINOPHENYL ACETIC ACID, 22, 23 df-a-AMINO-a-PHENYLPROPIONIC ACID,... 

Baylis-Hillman adducts such as 55 and 56 derived from 2-nitrobenzaldehydes were shown to function as useful precursors to functionalized (1H)-quinol-2-ones and quinolines. Treatment of 55 and 56 with iron and acetic acid at 110 °C afforded 57 and 58, respectively <02T3693>. A variety of other cyclization reactions utilized in the preparation of the quinoline scaffold were also reported. An iridium-catalyzed oxidative cyclization of 3-(2-aminophenyl)propanols afforded 1,2,3,4-tetrahydroquinolines <02OL2691>. The intramolecular cyclization of aryl radicals to prepare pyrrolo[3,2-c]quinolines was studied <02T1453>. Additionally, photocyclization reactions of /rans-o-aminocinnamoyl derivatives were reported to provide 2-quinolones and quinolines <02JHC61>. Enolizable quinone and mono- and diimide intermediates were shown to provide quinolines via a thermal 6jt-electrocyclization <02OL4265>. Quinoline derivatives were also prepared from nitrogen-tethered 2-methoxyphenols. The corresponding 2-methoxyphenols were subjected to a iodine(III)-mediated acetoxylation which was followed by an intramolecular Michael addition to afford the quinoline OAc O... 

Substituted phenyl trisulfanes (4-R CeH4)2S3 with R = NO2, MeCO, EtOCO, MeS, MeO, and even NH2 have been prepared by reaction 1. Since amino groups would also be attacked by SCI2, this reaction was carried out in anhydrous acetic acid, resulting in protonation of the -NH2 group to -NH3+, which is less reactive towards SC. The bisacetate obtained is converted to bis(4-aminophenyl)trisulfane by reaction with sodium hydroxide. ... 

Ring closure of 2-aminophenyl methyl ketones to 4-methylquinazolin-2(l//)-ones with potassium cyanatc in aqueous acetic acid without isolation of the intermediate 2-ureidophenyl methyl ketone (cf. p 44) is illustrated by the synthesis of 5,6-dimethoxy-4-methylquinazolin-2(l//)-one (42). ... 

Chloropyrazine reacted with benzyl 7V-hydroxy-7V-phenylcarbamate [PhN(OH)-COOCHjPh] in ethanolic potassium hydroxide to give 5-(4 -benzyloxycarbonyl-aminophenyl)-2-hydroxypyrazine which with hydrogen bromide in acetic acid gave 5-(4 -aminophenyl)-2-hydroxypyrazine (990). 

This procedure has found wdde application in the synthesis of aromatic and heteroaromatic azides the yields are usually high and often quantitative. General procedures have been developed by Smith and co-workers the method of choice mainly being determined by the basicity of the amine involved or the solubility of its salts. Weakly basic amines, for example, are diazotized with amyl nitrite in an acetic acid-concentrated sulphuric acid mixture and aqueous sodium azide is subsequently added. Amines which form insoluble salts with common mineral acids zu e converted to the more soluble 2-hydroxyethanesulphonic acid salts prior to diazotization. This procedure has been applied in the diazotization of the N-(aminophenyl)phthalimides (254). Treatment of the resulting diazonium compounds (255) with hydrazoic acid and removal of the protecting phthalimido group affords the otherwise inaccessible azidoanilines (equation 134). Some representative examples of azides recently synthesized by these methods, are shown in Table 11. 

Polyfluoropolyacrylate 30% Pentadecafluorooctyl methacrylate 2% UV initiator 0.3% Dimethyl aminophenyl acetic acid 30 80" 4.40(1.64) ... 

The intermediate in the Gabriel-Posner synthesis of quinazolin-2(lH)-one (fusion of o-aminobenzaldehyde with excess of urea), was found to be o-ureidobenzylidene urea (19), which then cyclized on heating, or in the presence of acid, with elimination of urea. The intermediate reacted with aniline, iV-methylaniline, and N,V-dimethylaniline to form 4-p-aminophenyl, 4-p-methylaminophenyl, and 4-p-dimethylaminophenyl quinazolin-2(lH)-ones in an unusual manner. Several quinazolin-2(li/)-ones were prepared by converting o-acylanilines into o-ureidophenyl ketones followed by cycli-zation in acetic acid medium for long periods at 55°C. A novel modification of this cyclization involved a Curtius or Hofmann reaction on 2 -benzoyl-oxanilic acid chlorides (20 = Cl) or amides (20 = NH2), respectively. 

Diazotization of 4-[(4-aminophenyl)sulfonamido]-2,6-dimethyl pyrimidine 10, followed by coupling of the diazonium salt with ethyl 3-oxobutanoate 11a or l,3-diphenyl-l,3-propanedione lib, afforded hydrazones 12a,b. Reaction of hydrazone 12a with aminoguanidine nitrate in refluxing acetic acid yielded the pyrazol-3-one 13a in 55% yield (00JIC42) (Scheme 4). 

Dihydro-6-(4-nitrophenyl)-2/f-l,3,4-oxadiazin-2-one can be reduced to the 4-aminophenyl derivative in low yield (37%) with hydrogen and palladium-charcoal in acetone at room temperature <88CB887>. Likewise, reduction of 3,6-dihydro-5-(4-nitrophenyl)-277-l,3,4-thiadiazin-2-one to the 4-aminophenyl compound is possible with tin(II) chloride in a mixture of hydrochloric and acetic acids <91JAP(K)03261773>. 

The reductive cyclization of 2-nitrophenylselenoacetic acid (168) with iron and acetic acid yields 2/7-l,4-benzoselenazin-3(4//)-one (169) (Equation (38)) <30JPR336>. This product is also available by the annulation of zinc di(2-aminophenyl)selenide (170) through reaction with chloroacetic acid and hydrogen chloride in ethanol. When treated with phosphorus pentasulfide the corresponding thione (171) is formed, and this, with bromoacetone and perchloric acid, affords 1-methyl-thiazolo[2,3-c]-l,4-benzoselenazium perchlorate (172), the basis of some cyanine dyestuffs... 

Nitro substituents in dihydrodiazepinium salts can be reduced by means of iron and acetic acid without reduction of the dihydrodiazepinium ring for example, p-aminophenyl-substituted dihydrodiazepinium salts have been obtained in this way.28 Although 6-nitro groups can also be reduced by metal and acid, it is not a satisfactory method for the preparation of 6-aminodihydrodiazepinium salts since the products apparently form complexes with the metal. 6-Amino derivatives are most conveniently prepared by catalytic reduction of the related nitro compound using either... 

---