Patent ID: 6069277
Filing Date: 2000-05-30
Classification: C07C

Abstract:
A process to produce a mono amino, diamino or polyamino aromatic compound, which process comprises:(a) reacting at ambient pressure and a temperature of between about 0 and 50.degree. C. for between about 0.1 and 24 hr, an electrophilic aromatic compound: ##STR19## wherein Q.sup.1, Q.sup.2, Q.sup.3, X, Y, and Z are each independently selected from the group consisting of --CN, --NO.sub.2, --COR, --CO.sub.2 R.sub.1, --CONR.sub.2, --SO.sub.2 R, --SO.sub.3 H, --CF.sub.3, --F, --Cl, --Br, --I and --NH.sub.2, wherein R, R.sub.1, and R are independently selected from the group consisting of alkyl having one to six carbon atoms, with the proviso that at least one of Q.sup.1, Q.sup.2, Q.sup.3, X.sup.1, Y.sup.1, and Z.sup.1 is hydrogen,with an effective amount of reagent selected from:(i) 1,1,1,-trialkylhydrazinium salt wherein alkyl is selected from the group consisting of methyl, ethyl, propyl, butyl and benzyl and the anion is selected from the group consisting of chloride, bromide, iodide, fluoride, sulfate, hydroxide, mesylate, triflate, and tetrafluoroborate,(ii) hydroxylamine,(iii) O-alkyl hydroxyl amine where alkyl is C.sub.1 to C.sub.10 carbon atoms, or(iv) 4-amino-1,2,4-triazole; and combinations thereof, in the presence of tetraalkyl guanidine wherein alkyl is C.sub.1 to C.sub.10 ;or the presence of a strong base selected from the group consisting of sodium butoxide, potassium butoxide, potassium propoxide, sodium propoxide, sodium ethoxide, potassium ethoxide, sodium methoxide, potassium methoxide, and combinations thereof;in a solvent selected from the group consisting of methanol, ethanol, propanol, butanol, dimethylsulphoxide, N-methylpyrrolidone, hexamethylphosphoramide, dimethylformamide, dimethylacetamide and mixtures thereof, provided that when alcohols are present primarily DATB and picramide are formed; and(b) isolating the monoamino, diamino or polyamino aromatic compound produced.