2 methyl 5 ethyl aniline

The first reported example of enantioselective reductive amination was that of Blaser et al. at Solvias (Scheme 7.7) [2]. At the time, 1999, they were still tweaking the industrial process for metolachlor, the active ingredient of the herbicide Dual , and examined its synthesis via the reductive amination of methoxyacetone with 2 methyl 5 ethyl aniline (MEA, limiting reagent). Working at the 100 mmol scale, they showed that a very low loading of an Ir xyhphos complex, under 80 bar (1160 psi) H2, neat, 50 °C, and 14 h, were optimal. By doing so, a 76% ee with full conversion was achieved. 

In our studies to date, the compounds in which oral and dermal studies were done have shown qualitative similarities in urine metabolic patterns. This was noted in the methyl ethyl aniline, CGA-73102, methidathion and atrazine studies discussed in this paper. Thus, based upon our experience, there is no reason to believe that major metabolic differences occur due to oral vs. dermal treatment routes. As noted by Pannatier et al ( ), specific examples of skin metabolism are scarce, except for steroid hormones. 

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 ... 

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. 

Water with aniline, benzene, benzyl alcohol, carbon disulfide, carbon tetrachloride, chloroform, cyclohexane, cyclohexanol, cyclohexanone, diethyl ether, ethyl acetate, isoamyl alcohol, methyl ethyl ketone, nitromethane, tributyl phosphate or toluene. 

NOTE - Petrochemical plants also generate significant amounts of solid wastes and sludges, some of which may be considered hazardous because of the presence of toxic organics and heavy metals. Spent caustic and other hazardous wastes may be generated in significant quantities examples are distillation residues associated with units handling acetaldehyde, acetonitrile, benzyl chloride, carbon tetrachloride, cumene, phthallic anhydride, nitrobenzene, methyl ethyl pyridine, toluene diisocyanate, trichloroethane, trichloroethylene, perchloro-ethylene, aniline, chlorobenzenes, dimethyl hydrazine, ethylene dibromide, toluenediamine, epichlorohydrin, ethyl chloride, ethylene dichloride, and vinyl chloride. 

FIGURE 6.16 Rp values of aromatic amines obtained on silica gel plate 1, 3 — isocratic development with 5 and 50% solutions of methyl ethyl ketone in cyclohexane, respectively, 2 — two-stepwise gradient development with both solvents open squares, N, N-dimethyla-niline, open triangles, iV-ethylaniline, open circles, aniline, diamonds, 2-phenylenediamine, filled squares, 3-phenylenediamine, filled triangles, 4-phenylenediamine, filled circles, 3-aminopyridine. (From Soczewinski, E. and Czapinska, K., J. Chromatogr. 168, 230-233, 1979. With permission.)... 

PEER polymers can be cured with traditional radical initiators such as methyl ethyl ketone (MEK) peroxides and benzoyl peroxide (BPO). Curing can be carried out either at room temperature or at elevated temperature. A PEER polymer containing 30 % maleic anhydride can be cured at room temperature with MEK peroxides in 10 to 60 min, depending on the type of peroxide used (Table 22.2). To cure a PEER resin with MEK peroxides at room temperature, a co-catalyst is needed. The commonly used cobalt naphthenate works very well in this case, while another co-catalyst, dimethyl aniline, is very efficient for the BPO system. 

Nitro-N-Etbyl-N-Metbyl Aniline, 02NCHflH4N(CH3XC2H mw 180.21, N13.55% crysts, mp 88° Prepd by beating diethylsulfate with 2-nicro-N,N-dim ethyl aniline to give the quaternary anilinium ethyl sulfate salt which was then heated to give the N-Eihyl-N-Methyl compound 1... 

Acetone, methyl ethyl ketone (2-butanone) and methyl isobutyl ketone (4-methyl-pentan-2-one) (6.8 mmol/kg bw for 3 days) increased the hepatotoxicity of carbon tetrachloride to Sprague-Dawley rats (Raymond Plaa, 1995a) this enhancement of toxicity was coincident with increased microsomal aniline hydroxylase activity (Raymond Plaa, 1995b). In addition to the effect on cytochrome P450, acetone, but not the other ketones, increased basal canalicular membrane fluidity, as measured by fluorescence polarization of 1,6-diphenyl-1,3,5 -hexatriene or 1 - [4-(trimethylammoniumphenyl)-6-phenyl] -1,3,5 -hexa-triene (Raymond Plaa, 1996). 

Fig. 5. The effect of germanium promotion on the activity and deactivation of hematite in the vapour phase methylation of 2-ethyl aniline by methanol.

Methyl 6 ethyl aniline see 2 Ethyl 6 methyl aniline... 

Isocyanates methyl ethyl phenyl etc. Phosgene + amine methylamine ethylamine aniline etc. 

Cesium-exchanged zeolite X was used as a solid base catalyst in the Knoevenagel condensation of benzaldehyde or benzyl acetone with ethyl cyanoacetate [121]. The latter reaction is a key step in the synthesis of the fragrance molecule, citronitrile (see Fig. 2.37). However, reactivities were substantially lower than those observed with the more strongly basic hydrotalcite (see earlier). Similarly, Na-Y and Na-Beta catalyzed a variety of Michael additions [122] and K-Y and Cs-X were effective catalysts for the methylation of aniline and phenylaceto-nitrile with dimethyl carbonate or methanol, respectively (Fig. 2.37) [123]. These procedures constitute interesting green alternatives to classical alkylations using methyl halides or dimethyl sulfate in the presence of stoichiometric quantities of conventional bases such as caustic soda. 

The synthesis of racemic metolachlor was accomplished by condensation of 2-methyl-6-ethyl-aniline (MEA) with methoxyacetone, followed by Pt/C reduction and chloroacetylation according to Figure 16. 

The use of PPF-OMe (3) also allowed the coupling of secondary alkylary-lamines that possess alkyl groups other than methyl. The reaction of AT-ethyl-aniline and 5-bromo-meta-xylene proceeds in excellent yield with no reduced arene formation, Eq. (26). It should be noted that the 3/Pd-catalyst system tolerates the use of CS2CO3 as base. 

Dimethyl-3-oxo-3,4-dihydro-E9a, 486 (Li - CH3) 2-Ethyl-3-oxo- E9a, 460 (2-SH-anilin + R-CHBr-COOR) 1,3-Benzothiazol 2-(l-Hydroxy-1 -methyl-ethyl)- E19d, 692 (H - Li/ + Keton)... 

Benzoyl peroxide, C HsCO-O-O-COCtHg, or methyl ethyl ketone peroxide, CH3C2Hs-C(0-0) CCzH5 CH3 is used as a catalyst. To initiate the reaction at room temperature it is necessary to add another substance ouch as cobalt naphthenate, (Cdimethyl aniline, C H (CH3), to produce an initiator, e.g. free radicals C6H C 00(benzoil radical). 

---