O-ETHYLANILINE

Formic acid is a good reducing agent in the presence of Pd on carbon as a catalyst. Aromatic nitro compounds are reduced to aniline with formic acid[100]. Selective reduction of one nitro group in 2,4-dinitrotoluene (112) with triethylammonium formate is possible[101]. o-Nitroacetophenone (113) is first reduced to o-aminoacetophenone, then to o-ethylaniline when an excess of formate is used[102]. Ammonium and potassium formate are also used for the reduction of aliphatic and aromatic nitro compounds. Pd on carbon is a good catalyst[103,104]. NaBH4 is also used for the Pd-catalyzed reduction of nitro compounds 105]. However, the ,/)-unsaturated nitroalkene 114 is partially reduced to the oxime 115 with ammonium formate[106]... 

Olive, J.-L. Biyoko, S. Moulinas, C., and Geneste, P., Hydroprocessing of Indole and o-Ethylaniline over Sulfided CoMo, NiMo, and NiW Catalysts. Appl. Catal, 1985. 19 pp. 165-174. 

The usefulness of palladium-based chemistry is highlighted by the multicomponent cascade reaction sequence that uses o-ethylanilines, aryl iodides, primary amines, and carbon monoxide (Equation 99) <2005JOC6454>. 

Fig. 5.5. GC separation of TFA derivatives of arylamines. Peak 1 = solvent (CH2CI2) 2 = N-methyl-aniline 3 = N,N-dimethylaniline 4 = N-ethylaniline 5 = N-methyl-o-toluidine 6 = N-methyl-m-toluidine 7 = N-methyl-p-toluidine 8 = o-toluidine 9 = o-ethylaniline 10 = aniline 11 = 2,5-dimethyl-aniline 12 = 2,6-dimethylaniline 13 = 2,4-dimethylaniline 14 = m- toluidine 15 = p-toluidine 16 = 2,3-dimethylamline 17 = 3,5-dimethylaniline 18 = m-ethylaniline 19 = p-ethylaniline 20 = 3,4-dimethylaniline. Conditions stainless-steel column, 18 ft. X 0.125 in. O.D., 9.5% Apiezon L + 3.6% Carbowax 20M on Aeropack 30 (80—100 mesh) helium flow-rate, 100 ml/min column temperature, 152°C. (Reproduced from Anal. Chem., 39 (1967) 1188, by courtesy of the American Chemical Society.)...

C7H14 2,3,3-trimethyl-1 -butene 594-56-9 1.095E-h10 74.960 14083 C8H11N o-ethylaniline 578-54-1 9.810E-K09 77.760... 

C8H11N o-ethylaniline 578-54-1 gas 1.055 2 15571 C8H1802S dibutyl sulfone 598-04-9 in benzene 4.467 1... 

The influence of the H2S partial pressure on the reactivity of aromatic amines has not received much attention in the literature. The only indication we found comes from a study of Yan et al. [22]. They noticed that the addition of H2S slightly decreased the conversion of o-ethylaniline. 

Active manganese dioxide seems to be the reagent of choice, having been used for conversion of many arylamines (e.g., aniline, m- and p-chloroaniline, o- and /7-anisidine, o-ethylaniline) into azo compounds in 90% yield. 

This synthesis always involves diazotization of an o-ethylaniline derivative followed by spontaneous cyclization. The following examples, classified according to the type of substrate, illustrate the procedures employed. Fused cinnoline-shave been made likewise. " ... 

The enantioselective reaction of lithiated N-pivaloyl-o-ethylaniline with various electrophiles was also successful [98] (Table 10). The temperature of the reaction significantly influenced the stereoselectivity. The reaction of lithiated N-... 

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