Ethyl aniline

Secondary and tertiary amines are not generally prepared in the laboratory. On the technical scale methylaniline is prepared by heating a mixture of aniline hydrochloride (55 parts) and methyl alcohol (16 parts) at 120° in an autoclave. For dimethylaniline, aniline and methyl alcohol are mixed in the proportion of 80 78, 8 parts of concentrated sulphuric acid are added and the mixture heated in an autoclave at 230-235° and a pressure of 25-30 atmospheres. Ethyl- and diethyl-anihne are prepared similarly. One method of isolating pure methyl- or ethyl-aniline from the commercial product consists in converting it into the Y-nitroso derivative with nitrous acid, followed by reduction of the nitroso compound with tin and hydrochloric acid ... 

Amines can be N-alkylated by reaction with alcohols, in a sealed tube with irradiation by microwaves, with the alcohol and RuCl2(PPh3)2, or by treatment with the amine, SnCl2 and Pd(PPh3)4. Chlorodiethylaluminum (Et2AlCl), with a Cu(ll) catalysts can N-ethylate aniline derivatives. tcrt-Butylamines can be prepared from isobutylene, HBr and the amine by heating a sealed tube. ... 

Silicontetrabromide 138 dealkylates amines such as diethylaniline into ethyl bromide and the adduct 139 (Scheme 3.13), which is readily hydrolyzed into ethyl-aniline [71]. 

For a general, simple high yield indole synthesis from anilines and methylthioacetaldehyde etc. see JACS 95,588,591,2718,6508 (1973). For indoles from N-( /3 -hydroxy-ethyl aniline esters see BSC 2485(1973). For a 2-acyl-indoles in one step from orthoamino-ketones and alpha-haloketones or 2-carboxyindoles from sulfonamides of ortho-aminocarbonyls see JOC 38,3622-24(1972). Indole and 5-Br-indole in 4 steps from beta-naphthol see Chem. Het. Cpds. (Russ.) 753(1973). Indole-JOC 37,3622(1972). 

FIGURE 2.12 Influence of pH value on retention of basic analytes. Samples A,A-dimethyl aniline A-ethyl aniline. Column symmetry shield CIS mobile phase acetonitrile-20 mM phosphate buffers-water, 35-35-... 

FIGURE 2.20 Characterization of RP columns for polar and silanophilic activity. Silanophilic activity asymmetry of p-ethyl aniline. Conditions as in Figure 2.8. Polar activity relative retention of hutylparabene and dipropylphthalate. Conditions as in Figure 2.19. 

NjH4 H20/Pd—C/C2HsOH 20-25 bis zum Verschwinden der Triibung, dann filtrieren 2. N2H4 H20/Raney-Ni zum Filtrat 50-55° bis zum Verschwinden der Triibung 4-(2-Amino-ethyl)-anilin O O 7 2... 

Na[BH4]/CoCl2 6H20/CH30H 40 1 h 4- (2-Amino-ethyl) -anilin 50 3... 

Mit Chlorbenzol oder Toluol entstehen bei der gleichen Reaktion Gemische von isomeren Aminoalkylierungsprodukten. Bei Verwendung von nur 1,5 Aquivalenten Aluminiumchlorid erhalt man aus 2-Oxo-l-phenyl-1,3-oxazolidin unter Ringoffnung nur N-(2-Chlor-ethyl)-anilin (48%). 

Anilin wird durch Essigsaure/Natrium-boranat bei 20° zu N-Ethyl-anilin (88%) alkyliert und bei 50-60° zu N,N-Diethyl-anilin (74%)1. 

FXrN" A ICas) [groDcr Oberschufi an Oxian] HjO 70% 4 5 h 4-Fluor-N,N-bis-[ 2-hydroxy-ethyl -anilin 61 5... 

In ahnlicher Weise erhalt man z. B. Dehydroakietylamin (86%) aus dem N-Benzyl-Derivat sowie N-Ethyl-anilin (82%) aus N-Benzyl-N-ethyl-anilin. 

Note N-Ethylaniline should not be confused with ortho-, meta- and para-Ethyl anilines, C2H5.CdH4.NH2, described here under Ethyl-phenylamines, that are called also Amino-ethylbenzenes... 

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