4- Chloro aniline

The reactivities of compounds of type 6 with aniline in acetone correlate quite well with substituent effects, and autocatalysis is unimportant here. In the less polar tetrahydrofuran, where the hydrochloride is only partly soluble, the reaction shows autocatalysis when aniline and -chloro aniline are reactants but not when the more basic -toluidine is involved. In these cases the solubility of the acidic product may also influence the differential behavior observed. 

Carbethoxycyclohexanone, 46, 82 2-Carbethoxycyclononanone, 47, 22 2-Carbethoxycyclooctanone, 47, 20 2-Carbomethoxycyclopentanone, conversion to 2-benzyl-2-carbometh-oxycyclopentanone, 45, 8 Carbon disulfide, reaction with /i-chloro-aniline and aqueous ammonia,... 

Benzenamine, 2-chloro- [Aniline, 2-chloro-], p-brommation of, 55, 23 Benzenamine, 3 chloro [Aniline, 3-chloro-J, p-bromination of, 55, 23 Benzenamine, jV.W-diethyl- [Aniline, N,N-diethyl-], p bromination of, 55, 23 Benzenamine, jV.A -dimcthyl [Aniline, N,N-dimethyl-], p-bromination of, 55, 23 Benzenamine, 2 3-dimethyl- [Aniline, 2,3-dimethyl-], p-bromination of, 55, 23 Benzenamine, 2,5-dimethyl- [Amhne, 2,5-dimethyl-], p-bromination of, 55, 23... 

Fig. 1 Reflectance scans of a chromatogram track with 100 ng each of 1 = 2,4-diamino-6-methylphenol, 2 = 3-chloro-4-methoxyaniline, 3 = aniline, 4 = 4-bromoaniline, 5 = 3-chloro-aniline, 6 = 2,6-dimethylaniline, 7 = 2-methyl-6-ethylaniline and 8 = 2-chloroaniline.

It is assumed that an excited state charge transfer complex is formed between the nitroaromatic in its first triplet state and the respective substrate. Internal proton transfer is immediately followed by hberation of carbon dioxide. Finally hydrolysis of the hemiacetal Ar —X—CH2OH (X = NH or S) leads to 2-chloro-aniline or thiophenol, respectively. In the decarboxylation of a-phenylthio-acetic acid, some methyl-phenylsulfide is also formed. (7t,7r )-nitroaromatics are more reactive than nitro compounds with lowest (n,7t )-triplets iso). 

The experimental procedure can be varied by the use of reagents which will give biguanides in situ and thus form the required triazine. Examples include 493, 554) the interaction of arylamines (e.g. p-chloro-aniline hydrochloride) and cyanoguanidine, followed by acetone and hydrochloric acid. Acetone may be replaced by its bisulphite compound, by diethyl acetal or by isopropenyl acetate, but p-chlorophenylbiguanide fails to condense 113) with acetone diethyl acetal at 130°. Under the correct acid conditions, the isomeric p-chloroanilino-triazine (CXXV) is not formed on the other hand, the free p-chlorophenylbiguanide base did not react with acetone in the absence of a catalyst. 

Chlorotrifluoromethyl aniline (no. 73.) was found in the sediment samples. This compound is used as a reactant with chloro-aniline (no. 72) in the preparation of 4,4 -dichloro-3-(trifluoromethyl)-carbanilide, a disinfectant. Two other related compounds also found in some of the sediments were chlorophenyl isocyanate (no. 74) and chloro(-trifluoromethyl)phenyl isocyanate (no. 75). This suggests that some of the 4,4 -dichloro-3-(trifluoromethyl)-carbanilide may, in fact, exist in the sediment extracts but is decomposed in the injection port of the gas chromatograph, since it is very doubtful that the easily hydrolyzable isocyanates exist as such in the sediments. To strengthen this hypothesis some 3,4,4 -trichlorocarbanilide [none of the 4,4 -dichloro-3-(trifluorome-thyl)-carbanilide was available] was analyzed by GCMS. The injection port temperature was 300°C. As expected, none of the parent compound eluted from the column. However, mass spectra were obtained for chlorophenyl isocyanate, dichlorophenyl isocyanate, chloroaniline, and dichloroaniline. The presence of the carbanilides themselves (no. 76, 77, 78) was confirmed with the help of HPLC and mass spectral identification. 

Figure 637 Stop flow spectra obtained from a 3,4-difluoro impurity with RRT 1.5 (0.5% by area) in a drug substance containing a 3-fluoro, 4-chloro aniline functional group. Acquisition time was for (a) 2 h and (b) 30 min. Spectra were acquired on a Bruker DRX500 fitted with a 4-mm SEI z-gradient EC probe with a 120 pi active cell volume.

Use of a large, lipophilic nitrogenous component results in a 1idocaine like, local anesthetic type cardiac anti-arrhythmic drug, lorcainide (20). Synthesis begins with the Schiff s base (1 ) derived by reaction of p-chloro-aniline and borohydride followed by acylation with phenyl acetyl chloride produces amide 1 . Selective hydrolysis with HBr followed by alkylation with isopropyl bromide completes the synthesis of lorcainide (20). ... 

Dinitro-2,2 -dichloroazobenzene. brn-red prisms (from solv naphtha), mp 274°(Ref 1) or red ndls (from benz), mp 265°(Ref 3), mp 275-76° (Ref 4) readily sol in benz mod sol in glac acet acid si sol in acet insol in ale was prepd by oxidization of 4-nitro-2-chloro-aniline with alk Na hypochlorite soln (Ref 1) and in 87% yield by oxidation of 4-nitro-2-chloroaniline with iodosobenzene diacetate at 35°(Ref 5)... 

Figure 14.11 Reduction of NACs in ferrogenic aquifer solid columns. Concentrations of 4-chloronitro-benzene (4-C1-NB, ) and of its transformation product 4-chloro-aniline (4-Cl-An, o) vary with position (and time) in the column. Also indicated is the excellent mass balance (a). Adapted from Heijman et al. (1995).

Pigment Orange 36 [12236-62-3] 11780 monoaZo benzimid- azolone coupling of diazotized 2-nitro-4-chloro-aniline with acetoacetyl-5-amino-benzimidazolone... 

Using the two most effective modifiers the reaction stops after consumption of the theoretical amount of hydrogen. This is indicated by a sharp decrease of the catalyst potential and no further hydrogen uptake. In the case of the 2-chloro aniline no dehalogenated products are detectable by GLC even after prolonged hydrogenation times. 

Trinitro-3-chloroaniline under Chloro-aniline and Derivatives... 

In the triazolopyridine series it has been observed19 that a chloro substituent in an ortho position to the methyl group of tolyl heterocycles exerts an additional activating effect. Thus, in the case of triazolopyridine (19), reaction with Schiff s base from benzaldehyde and p-chloro-aniline yields the expected stilbene (20), whereas no reaction is observed in the case of the analog lacking the chlorine atom. 

Besides benzalanilines, also anils derived from heterocyclic aldehydes may be employed (Table VI), as, for example, in the reactions of 4,5-diphenyl-2-(p-tolyl)oxazole (58) with SchifFs bases from p-chloro-aniline and 3-formylpyridine and 2-formylthiophene, leading, respectively, to the /3-(3-pyridyl)-4-(4,5-diphenyloxazol-2-yl)styrene (59) 33 and the /S-(2-thienyI) analog (60).11... 

Further styryl and stilbenyl derivatives from 90 and 91 are shown in Table VII. Also reaction of these two compounds with heteroaromatic anils, such as that derived from 3-formyldibenzofuran and p-chloro-aniline, leads to the formation of the styryl and ethylene compounds 94 and 95, respectively.54... 

It was also established that Schiff s bases derived from />-chloro-aniline are especially reactive toward 2-(p-tolyl)naphtho[l,2-6 ]triazole.68... 

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