4- Bromo-3-nitroaniline

C6H5BrN202 4-bromo-3-nitroaniline 53324-38-2 25.00 1.7656 2 6833 C6H5N03 3-pyridinecarboxylic acid 1-oxide 2398-81-41 53.33 1.3510 2... 

An important reaction parameter is the choice of the base and NajCO or NaOAc have been shown to be preferable to EtjN in some systems[2]. The inclusion of NH4CI has also been found to speed reaction[2]. An optimization of the cyclization of A -allyl-2-benzyloxy-6-bromo-4-nitroaniline which achieved a 96% yield found EtjN to be the preferred base[3]. The use of acetyl or inethanesulfonyl as N-protecting groups is sometimes advantageous (see Entries 4 and 5, Table 4.1). 

Fig. 1.11 Dissociation ranges of colour indicators for determination of the acidity function H0 in H2S04-H20 mixtures (1) p-nitroaniline, (2) o-nitroaniline, (3) p-chloro-o-nitroaniline, (4) p-nitrodiphenylamine, (5) 2,4-dichloro-6-nitroaniline, (6) p-nitroazobenzene, (7) 2,6-dinitro-4-methylaniline, (8) benzalacetophenone, (9) 6-bromo-2,4-dinitroaniline, (10) anthraquinone, (11) 2,4,6-trinitroaniline. (According to L. P. Hammett and A. J. Deyrup)...

Primaquine Primaquine, 8-[(4-amino-l-methylbutyryl)amino]-6-methoxyquinoline (37.1.2.4), is made from 6-methoxy-8-nitroquinoline (37.1.2.1), which is synthesized in a Skraup reaction from 4-methoxy-2-nitroaniline and glycerol in the presence of sulfuric acid. The nitro group in this compound is reduced to make 6-methoxy-8-aminoquinoline (37.1.2.2). Alkylating the amino group with 4-bromo-l-phthalimidopentane gives 8-[(4-phthalimido-l-methylbutyryl)amino]-6-methoxyquinoline (37.1.2.3), the hydrazi-nolysis of which removes the phthalimide protection, giving primaqnine [28,29]. 

The 1,5-Bis (o ), mp 209 (m.-), mp 244°, and (p-), mp 262° derivs were prepd by Braun Rudolph (Ref 2) by nitrating the parent compd with a l/l mist of fuming nitric acid + sulfuric acid on a water bath. Horwitz Gra-kauskas (Ref 4) prepd the l,5-Bis(p-dinitro) deriv by coupling diazotized p-nitroaniline with 1-acetyl-2-(4,-bromo benzoyl) hydrazine, separating the tetrazole following cyclization l-(m-Nitrophenyl)-5-(p-nitrophenyl)-tetrazole, crysts, mp 170° (Ref 2)... 

More important is the substitution of leaving groups in ortho positions to the diazonium moiety by water when other activating substituents are present on the aromatic ring. For example, 2-bromo-3,4,6-trifluoro- or 3,4,6-trifluoro-2-nitroaniline cannot be diazotized in water without extensive hydrolysis of the 2-substituent giving 4.193 This drawback can be overcome, to give 5, by performing the diazotization in acetone at — 20°C.3 193 194... 

See 3-Bromo-2,7-dinitro-5-benzo[/ ]thiophenediazonium-4-oxide See 4-Chloro-2-nitroaniline, below... 

The most important diazo components are 4-nitroaniline [100-01-6], 2-chloro-4-nitroaniline [121-87-9], 2-cyano-4-nitroaniline [17420-30-3], 2,4-dinitroaniline [97-02-9], 2,6-dichloro-4-nitroaniline [99-30-9], 2-bromo- [1817-73-8] and 2-chloro-4,6-dinitroaniline [3531-19-9], and 2-bromo-6-cyano-4-nitroaniline [17601-94-4], The coupling components are derived from aniline, 3-aminotoluene 1108-44-1], 3-chloroaniline [108-42-9], 3-aminoacetanilide [102-28-3], and 3-amino-4-alkoxyacetanilide by /V-alkylation. 

Bromo-4-nitro line 3-Bromo-4-nitroaniline Benzene A-l 30%. JS6 ... 

An apparent excbption to the favorable influence of an o-nitro group is found in 2-bromo-6-nitroaniline.28 The failure of the Bart reaotion on this compound may be due to steric hindrance. 

Although ortho-nitroanilines were introduced at an early stage as PPGs, this group was not extensively used as such [111]. In contrast, the cyclic version - the 7-nitroindolines - proved to be much more useful, in particular when it carried a 5-bromo substituent [112]. The reaction was seen to be quite rapid, even at wavelengths up to 400 nm, while the side product - the parent deacylated nitroindoline - was shown to be chemically and photochemically unreactive. Yet, it is typically appropriate for releasing carboxylic acids, as shown by the example of Merrifield in 1977 (Scheme 13.29) [113],... 

C7H7BrN202 2-bromo-6-methyl-4-nitroaniline 102170-56-9 25.00 1.6583 2 10640 C7H7N02 benzohydroxamic acid 495-18-1 37.08 1.2150 2... 

C7H8BrN 2-bromo-5-methylaniline 53078-85-6 520,51 45.859 2 10829 C7H8N203 4-methoxy-2-nitroaniline 96-96-8 463.98 40.434 2... 

This acid is obtained (1) By subjecting 2 bromo-5-nitroaniline to tlie Bart reaction, lire yield is 25 per cent. (2) Twenty-eight grams of... 

O2N.CaH4.NH.C6H4.NO2 golden-yel Ifts, mp 166—69°. It ean be prep from 2-nitroaniline and 2-bromo-l-nitrobenzene on heating in Na Carbonate soln with CujClg catalyst at 180° Refs 1) Beil 12, 690 (341) 2) P, Juillard,... 

T rinitrodiphenylamine, (02N)2CgH3.NH.CgH4.N02 yel ndls (from glac acet ac) or grn-yel crysts (from acet or pyridine), mp 193-95° readily sol in acet, glac acet ac acetic anhydride mod sol in benz, chlf, ale, eth CS2 si sol in petr eth was prepd by reaction of 4-chloro or 4-bromo-1,3-dinitrobenzene 3-nitroaniline, and by other methods (Refs 1 2)... 

Bromo-5-nitro line 2-Bromo-5-nitroaniline Benzene A-1 30% 38... 

Bromo-1,8-naphthalenedicarboxylic anhydride 1-Bromo-2-naphthol 4-Bromo-2-nitroaniline... 

TSCA 40CFR716.120.c4 aniline and chloro-, bromo-, and/or nitroanilines T120-C4... 

Hauser et were able to isolate the intermediate dimeric halide when 9-chlorofluorene was allowed to react with only one equivalent of sodium amide in liquid ammonia. In t-butyl alcohol containing its potassium salt or a dilute aqueous solution of benzyltrimethylammonium hydroxide, the rate of formation of bifluorenylidene is second-order in 9-bromofluorene and first-order in the basicity of the reaction medium as measured by the ionisation of nitroaniline indicators . Under the same reaction conditions, protium exchange of 9-deutero-9-bromofluorene and elimination from 9-bromo-9,9 -bifluorenyl are much faster reactions than the conversion of 9-bromofluorene into bifluorenylidene. These facts are consistent with the displacement mechanism. 

The Doebner-von Miller reaction was used as a method of choice for the synthesis of several biological active quinoline compounds. The anti-malarial drug primaquine, which acts against the hepatic stage of plasmodia infection, was synthesized by a Skraup reaction fi om 4-methoxy-2-nitroaniline and glyceron in the presence of sulfiiric acid. The nitro group was then reduced and alkylated with 4-bromo-l-phthalimidopentane to provide the protected primaquine, which was deprotected by using hydrazine. ... 

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