Ethyl naphthylamine

Thus good yields (> 60 per cent) are obtained with aniline and methyl, ethyl, n-propyl and n-butyl phosphates with a- and P-naphthylamine and methyl or ethyl phosphate nuclear substituted anilines and methyl or ethyl phosphate. 

Methylaniline Ethylaniline n-Propylaniline n-Butylaniline Benzylaniline 2 -MethyIbenzylamine N-Ethylbenzylamine 2 -Methyl o-toluidine N-Methyl m-toluidine 2 -MethyI p-toluidine N-Ethyl o-toIuidine N-Ethyl m-toIuidine 2S -Ethyl p-toluidine 2 -MethyI a-naphthylamine N-Methyl p-naphthylamine N-Phenyl- a-naphthylamine 2 -Phenyl-P-naphthylamine... 

Pigment Blue 1 [1325-87-7] 42595 2 triarylcarbonium PTMA salt (Victoria Blue B) condensation of 4,4 -bis-A/A/-dimethyl aminoben2ophenone with /V-ethyl-1-naphthylamine, followed by oxidation and salt formation... 

In the ketone method, the central carbon atom is derived from phosgene (qv). A diarylketone is prepared from phosgene and a tertiary arylamine and then condenses with another mole of a tertiary arylamine (same or different) in the presence of phosphoms oxychloride or zinc chloride. The dye is produced directly without an oxidation step. Thus, ethyl violet [2390-59-2] Cl Basic Violet 4 (15), is prepared from 4,4 -bis(diethylamino)benzophenone with diethylaruline in the presence of phosphoms oxychloride. This reaction is very useful for the preparation of unsymmetrical dyes. Condensation of 4,4 -bis(dimethylamino)benzophenone [90-94-8] (Michler s ketone) with AJ-phenjl-l-naphthylamine gives the Victoria Blue B [2580-56-5] Cl Basic Blue 26, which is used for coloring paper and producing ballpoint pen pastes and inks. 

Ethyl methacrylate [97-63-2] M 114.2, b 59 /100mm, d 0.915, n 1.515. Washed successively with 5% aqueous NaN02, 5% NaHS03, 5% NaOH, then water. Dried with MgS04, added 0.2% (w/w) of phenyl-6-naphthylamine, and distd through a short Vigreux column [Schultz J Am Chem Soc 80 1854 7958]. 

Ethy Ibenzy lamine A -Methyl o-toluidine A -Methyl m-toluidine. 2V-Methyl p-toluidine A -Ethyl o-toluidine -Ethyl m-toluidine -Ethyl p-toluidine 2V-Methyl a-naphthylamine 2V-Methyl p-naphthylamine 2V-Phenyl- a-naphthylamine N-Phenyl- p-naphthylamine... 

Arylazo-l-naphthylamines were first reacted with ethyl orthoformate in boiling xylene for 2 hr diethyl malonate and piperidine were then slowly added to the reaction mixture over a period of 15-20 min. The resulting... 

Anilines, bis(2-amino-4-chlorophenyl)disulfide, naphthylamine, 2- and 3-aminopyridines, 2-aminopyrimidines, 2-, 3-, 5-, 6-, 7-, and 8-aminoquino-lines, 6-aminocoumarin, and 2-aminopyrazine were reacted in the absence or presence of a solvent (ethanol, toluene) with ethyl orthoformate and isopropylidene or 4-heptylidene malonates to give alkylidene (het)aryl-aminomethylenemalonates (442, R = R2 = Me, Pr) in 32-100% yields [69BRP1147759 75USP3907798 88JAP(K)239269]. p-Toluenesulfonic acid monohydrate was sometimes applied as catayst. 

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... 

Under similar conditions, secondary aromatic amines, such as JV-ethyl-1-naphthylamine, may also be nitrosated directly. 

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... 

V-Ethylbenzylamine A -Methyl o-toluidine TV-Methyl m-toluidine. A7-Methyl p-toluidine A7-Ethyl o-toluidine A7-Ethyl m-toluidine A7-Ethyl p-toluidine A7-Methyl a-naphthylamine. . ZV-Methyl p-naphthylamine. 2V-Phenyl-a-naphthylamine. N-Phenyl- p-naphthylamine. ... 

For benzo[c]pyrylium salts having different alkyl substituents in positions a(l) and a (3), the reaction with secondary amines loses its predictable regioselectivity. Thus, reaction with dimethylamine, independent of the solvent, gives rise to /3-naphthylamine 185, from l-ethyl-3-methyl-substituted salt 183 (81KGS1608), and a-naphthylamine 186 from 1-benzyl derivative 184 (88UP1). In the former case, the nucleophilic attack occurs in position 3, whereas in the latter case, it takes place in position 1. 

Conversion of stabilized diazo compounds to hydrocarbons does not depend upon the reducing action of ethyl alcohol, for the reaction takes place smoothly in acetone, ether, nitrobenzene, benzene, chloroform, apd carbon tetrachloride. No acetaldehyde is produced when ethanol is the solvent. In the absence of metals, however, when the stabilized salts of diazotized a-naphthylamine are treated with ethyl alcohol, acetaldehyde, naphthalene, a-ethoxynaphthalene, and tar are obtained. 

The iV-methylamine (160) (R = Me) gives a complex mixture of products when treated under the same conditions.186 It was shown subsequently that prior reduction of the anils used as starting materials is, in fact, unnecessary since in the presence of potassamide in liquid ammonia (o-chlorobenzylidene)aniline forms phenanthridine in excellent yield, and the analogous anils from p-toluidine and a-naphthylamine undergo ring closure under similar conditions. In view of the known trans geometry of the anils and the unlikelihood of trans-cis equilibration under these conditions this reaction deserves further study.187 Potassamide in liquid ammonia also converts 2-bromo-iV-ethyl-3 -hydroxybenzanilide (162) into a mixture of iV-ethyl-3-(164) and N-ethyl-1 -hydroxyphenanthridone (165), probably via the aryne (163).188... 

Also IV-ethyl-l-naphthylamine reacts with 2-methylthio-1,3-dithiolylium iodide (195) to form the 1,3-dithiolylium salt (212) which can be dehalogenated with base to the quino-methidimine derivative (213) (81CC565). 

Similarly, (V-ethyl-l-naphthylamine was prepared in 88% yield, and (V-ethyl-, N-bu-tyl- and (V-benzyl-2-naphthylamine, and (V-ethyl- and (V-butyl-/ -toluidine were prepared in 50-64% yields.34 In the alkylation of / -toluidine and / -anisidine with butyraldehyde, N,N-dibutyl derivatives were also produced in 19 and 25% yields, respectively. The Emerson-Waters procedure was also applied to the reductive alkylation of 2-phenylpropylamines and 2-phenylisopropylamines with C1-C3 aldehydes (amine aldehyde ratio = 1 3).35 With higher aldehydes the monosubstituted products were isolated in good yields (in 48-94% yields with acetaldehyde), while with formaldehyde (V.N-dimethyl derivatives were obtained in 51-85% yields. 

Up to the present the only method used for the reduction of 0-naphthylamine for obtaining the tetrahydro base has been with sodium and alcohol. This method was first described by Bamberger and Muller.2 It is possible to substitute ethyl alcohol for amyl alcohol but the yield is distinctly lower. The base has been resolved into its optically active components.3... 

---