1- Chloro-2-naphthylamine

Acridine and compounds Aniline and compounds Benzanthrone and compounds Benzidine and compounds Chloro compounds Naphthalene and compounds Naphthylamines Nitro compounds... 

From photoreduction (> 280 nm) in diethylamine, low yields of 1-naphthyl-amine and the corresponding azo- and azoxy compounds have been obtained Photolysis (366 nm) in acidified 50% aqueous 2-propanol at varied HCl-concentrations results in remarkable enhancement of photoreduction compared to neutral 2-propanol. The highest disappearance quantum yield measured was 1.28 X 10 2 for 6 M HCl 4-chloro-l-naphthylamine is formed as main product 74.75). 

The use of trialkyl phosphates for dialkylation of anilines has been found applicable to naphthylamines and to a large number of anilines substituted in the ortho, meta, or para position by groups such as chloro, methoxy, and methyl and in the meta position by fluoroalkyl (author s laboratory). The reaction has been used to introduce ethyl and M-butyl as well as methyl groups by employing the appropriate phosphate esters. The reported yields range from 50% to 95%. 

AI3-00040, see Cyclohexanol AI3-00041, see Cyclohexanone AI3-00045, see Diacetone alcohol AI3-00046, see Isophorone AI3-00050, see 1,4-Dichlorobenzene AI3-00052, see Trichloroethylene AI3-00053, see 1,2-Dichlorobenzene AI3-00054, see Acrylonitrile AI3-00072, see Hydroquinone AI3-00075, see p-Chloro-rrr-cresol AI3-00078, see 2,4-Dichlorophenol AI3-00085, see 1-Naphthylamine AI3-00100, see Nitroethane AI3-00105, see Anthracene AI3-00109, see 2-Nitropropane AI3-00111, see Nitromethane AI3-00118, see ferf-Butylbenzene AI3-00119, see Butylbenzene AI3-00121, see sec-Butylbenzene AI3-00124, see 4-Aminobiphenyl AI3-00128, see Acenaphthene AI3-00134, see Pentachlorophenol AI3-00137, see 2-Methylphenol AI3-00140, see Benzidine AI3-00142, see 2,4,6-Trichlorophenol AI3-00150, see 4-Methylphenol AI3-00154, see 4,6-Dinitro-o-cresol AI3-00262, see Dimethyl phthalate AI3-00278, see Naphthalene AI3-00283, see Di-rj-butyl phthalate AI3-00327, see Acetonitrile AI3-00329, see Diethyl phthalate AI3-00399, see Tributyl phosphate AI3-00404, see Ethyl acetate AI3-00405, see 1-Butanol AI3-00406, see Butyl acetate AI3-00407, see Ethyl formate AI3-00408, see Methyl formate AI3-00409, see Methanol AI3-00520, see Tri-ocresyl phosphate AI3-00576, see Isoamyl acetate AI3-00633, see Hexachloroethane AI3-00635, see 4-Nitrobiphenyl AI3-00698, see IV-Nitrosodiphenylamine AI3-00710, see p-Phenylenediamine AI3-00749, see Phenyl ether AI3-00790, see Phenanthrene AI3-00808, see Benzene AI3-00867, see Chrysene AI3-00987, see Thiram AI3-01021, see 4-Chlorophenyl phenyl ether AI3-01055, see 1.4-Dioxane AI3-01171, see Furfuryl alcohol AI3-01229, see 4-Methyl-2-pentanone AI3-01230, see 2-Heptanone AI3-01231, see Morpholine AI3-01236, see 2-Ethoxyethanol AI3-01238, see Acetone AI3-01239, see Nitrobenzene AI3-01240, see I idine AI3-01256, see Decahydronaphthalene AI3-01288, see ferf-Butyl alcohol AI3-01445, see Bis(2-chloroethoxy)methane AI3-01501, see 2,4-Toluene diisocyanate AI3-01506, see p,p -DDT AI3-01535, see 2,4-Dinitrophenol AI3-01537, see 2-Chloronaphthalene... 

Naphthylamine, 4-aminodiphenyl, 4-chloro-2-toluidine, benzidine, 2,4,5-trimethylaniline, 2,4-diaminoanisol, 2,4-toluylenediamine, 2-amino-4-nitrobenzene, 3,3 -dichlorobenzidine, 3,3 -dimethoxybenzidine, 3,3 -dimethylbenzidine, 3,3 -4,4 -diaminodiphenylmethane, 4,4 -diaminodiphenybnethane, 4,4 -methylene-bis-(2-chloroaniline), 4,4 -Oxydianiline, 4,4 -thiodianiline, 2-aminoazotoluene,... 

Co-exposures 4,4 -Methylene bis (2-methylaniline) (2B) Magenta (2B) Safranine T or/ oNitrotoluene (3) 2,5-Diaminotoluene (3) Aniline (3) ori/io-Amino-azotoluene (2B) Multiple ejqjosures including 4-chloro-o/t/io-toluidine and 4-chloroacetyl-or/Zio-toluidine A/ Acetyl-or//io-toluidine 6-Chloro-or//io-toluidine 4-Chloro-or//io-toluidine (2A) Aniline (3) Hydroquinone (3) Toluene (3) Carbon disulfide Sulfur Benzothiazole 4-Aminobiphenyl (contaminant) (1) 2-Mercaptobenzothiazole (Ward et al, 1996) (Proprietary chemical) Aniline (3) 2-Mercaptobenzothiazole Phenyl-p-naphthylamine (3)... 

Nitro-2-diazo- 1-napbtbol, crysts (from benz), mp 187° (dec) was prepd by diazoti2ation of l-chloro 3-Nitro-2-naphthylamine and pouring the diazonium soln in aq Na acetate (Ref 9) 6-Nitrot2-diazo-l napbtbol [called 6-Nitro-2-... 

Ref 4). Was first prepd by Staedel(Ref 2) by heating the ethyl ether of 2,4,5 trinitro-o-naphthylamine with ale NHS in a sealed cube at 50° for 2 hours. A simpler method is to pass NHS gas through an amyl alcohol soln of 4 chloro-l,3,8 trinitro-naphthalene (Ref 3). Other methods are described in Ref 4... 

Studies (2, 3) have also been reported of the reaction of phosphorus trichloride with diarylamines containing p-methyl or p-chloro substituents. In every case, the expected ring-substituted derivatives of 1 and 2 were obtained after the reaction mixture was treated with water. The interaction of (V-phenyl-o-toluidine and phosphorus trichloride at 200°C also gave a reaction mixture from which the expected phosphine oxide was isolated (3). None of the corresponding spirophosphonium chloride, however, could be obtained. The failure to isolate this substance can not be explained simply by the presence of an ortho substituent in the diarylamine, since it had been previously found that a 34% yield of a spirophosphonium chloride can be obtained via the interaction of fl/-phenyl-l-naphthylamine and phosphorus trichloride (2). No dihydropheno-phosphazine derivatives at all were obtained by the interaction of di-o-tolylamine and phosphorus trichloride at 200°C (3). 

Dinitronaphthalene ( Gamma-dinitronaph-thalene, 1,3-DNN). Bright yel needles from aq pyridine, mp 144°, bp subl (Refs 1 32) CA Registry No 606-37-1. It is prepd by the action of nitric ac/sulfuric ac on naphthalene at low temps (Refs 14 33) by the nitration of 1-MNN with a mixt of 17.3% nitric ac, 61.2% sulfuric ac, and 21.5% w, temp 59—75°, time.90min (Ref 52) by the action of powd Cu (Ref 18) or hydrazine (Ref 22) on l-chloro-2,4-dinitro-naphthalene by the diazotization of 2,4-dinitro-1-naphthylamine followed by redn of the dia-zonium salt with EtOH (Ref 25) or by the action of Br on 5,7-dinitro-l,2,3,4-tetrahydro-naphthalene followed by dehydrobromination (Ref 13). It is used to prep more highly nitrated naphthalenes... 

C11H11N 3-methyl-2-naphthylamine 10546-24-4 20.86 1.0491 2 21930 C11H13CI03 4-(4-chloro-2-methylphenoxy)butanoic acid 94-81-5 25.00 1.2009 2... 

Condensation also takes place between arsenious chloride and jS-naphthylamine, di-)3-naphthylamine, or di-a-naphthylaminc (not with a-naphthylamine), to yield li-chloro-U 7-dihydrodibenzophetiarsaisine (VI) in the case of the 0-compounds, and 7-chloro-7 U-dihi/drod enzo-pltenarmzitie (VII) with the a-compound ... 

This method is essentially that described by Goldhahn. 4-Nitro-l-naphthylamine has also been prepared by the nitration of a-naphthylamine, acetyl-a-naphthylamine, and ethyl-1-naphthyloxamate, by the oxidation of 4-nitroso-l-naphthyl-amine, and by reaction of 4-chloro-l-nitronaphthalene with ammonia. ... 

Ion pair RP-HPLC with DA-UVD offers a good alternative for determination of mixtures of PAA which are difficult to resolve by usual RP-HPLC procedures. After optimization as for the pH and anionic component of the isocratic mobile phase, it was opted for phosphate buffer at pH 2.5, containing 5 mM of sodium 1-hexanesulfonate and MeOH in 65 35 volumetric proportion. The method was applied to detection of banned azo dyes, after reduction to PAA, of which the banned ones are denoted by (entries in Table 1 carrying note e). In a study involving 2-, 3- and 4- chloroaniline (lh), 2- (lb) and 4-toluidine (Id), 3-, 4- (2g) and 5-chloro-2-toluidine, 3-, 4- and 5- nitro-2-toluidine (2h), 2,3-, 2,4- (2e) and 2,6-diaminotoluene (2f), 1- (8a) and 2- naphthylamine (9a) under identical conditions, the isomers were well separated from each other, except for 2- and 4-toluidine which had distinct but close retention times with no baseline separation211. 

Dimethylchloromethylene ammonium chloride (dimethylformamide chloride) or the adduct from dimethylformamide and phorphoryl chloride adds to N-dimethyl-cyanamide, yielding dimethyl(2-aza-l-chloro-3-dimethylamino)allylidene ammonium chloride, isolated as perchlorate (7v)l02 The highly reactive chlorine in (7 v) is very readily substituted by bases and affords, with 0-naphthylamine, the guanidine derivative (253), which on heating cyclizes smoothly to 2-dimethylaminobenzo(f )quinazo-line (254) ... 

Several routes to benz[c]acridines involve electrophilic aromatic substitution to form the heterocyclic ring. Thus, 9-nitrobenz[c]acridine results from the cyclisation of the 2-(l-naphtlylamino)benzaldehyde derived from 1-naphthylamine and 2-fluoro-5-nitrobenzaldehyde (J. Rosevear and J.F.K. Wilshire, Austral. J. Qiem., 1981, 34, 839). The reaction between a ff-aryl-l-naphthylamine and acetic anhydride has been used to synthesise 9- and ll-hydroxy-7-methylbenz[c]acridines and cyclisation of partially reduced 2-(l-naphtltylamino)benzoic acid by phosphorus oxychloride affords the 7-chloro-l,2,3,4-tetralydro derivative (B.V. Lap et ai,y J. heterocyclic Chem., 1983, 20, 281). 

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