Meta-chloroaniline

Alkaline formaldehyde is also useful in removing the amino group of ortho- and pam-chloroanilines 50-55% yields of chlorobenzene are obtained. With 2,5-dichloroaniline, however, the yield falls to 10%. The formaldehyde procedure cannot be applied to nitroamines inasmuch as reduction of the nitro group occurs. Only a 20% yield of nitrobenzene is obtained from o-nitroaniline, and with the meta and para isomers the yield drops to 10%.4... 

Displacement chromatogram of a chloroaniline mixture containing 44.7 umol of the meta isomer, 29.8 umol of the ortho isomer and 16.4 umol of the para isgmer. Conditions 50 cm x 4.6 mm ID beta-cyclodextrin-silica column, carrier solvent 10 % v/v methanol water displacer 13 mM p-nitrophenol dissolved in the carrier solvent displacer flow-rate 0.2 mL/min column temperature 30 C. 

Phenylurea derivatives mono-halogen-substituted in meta position were found to undergo nearly quantitative photohydrolysis, in the same way as 3-chloroaniline this was evidenced for chlorotoluron [84,85] and for metoxuron [86], but also for the related carbamate derivative chlorpropham (isopropyl-3-chlorocarbanilate) [49]. 

AI3-12126 1-Amino-3-chlorobenzene m-Amino-chlorobenzene meta-Aminoohlorobenzene Aniline, m-chloro- Benzenamine, 3-chloro- CCRIS 3402 3-Chlooranilinen 3-Chloroaniline m-Chloraniline 3-Chlorobenzenamine m-Chloroaminobenzene 3-Chlorophenylamine m-Chlorophenylamine 3-Cloroaniline EINECS... 

Aromatic bases such as the toluidines, xylidines, chloroanilines, 1-naphthyl-amine, benzidine, and tertiary amines can be simply converted into their sulfonic acids by heating ( baking ) with ammonium hydrogen sulfate. This method has the advantage over normal sulfonation by sulfuric acid that exactly theoretical amounts can be used so that no higher sulfonation product is obtained. Further, isomers are rarely obtained, since the sulfo group almost always enters exclusively at the /rara-position or, if that is occupied, at the or/Ao-position, and never at the meta-position. 

Chloroaniline was replaced by one hundred and fifty ortho, meta and/or para substituted anilines using acetone as both the carbonyl conq>onent and the solvent. Again, substituents were chosen to test steric, electronic and lipophilic properties and all gave smooth product formation. Five- and six-membered heterocyclic amines were also explored and tended to give lower yields of less pure products. In some cases, die only product isolated derived fitim direct addition of the aminoheterocycle to BTF. Aliphatic amines failed in this reaction even using pre-formed enamines. 

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