An economic, one-step method for the production of N-substituted aromatic hydroxylamines of formula (I)
R—N(OH)—C(═O)—(O)R.sub.1  (I),
with hydrogen, by catalytic hydration with possibly modified hydration catalysts in an aprotic solvent and in the presence of a halogen formic acid ester and in some cases in the presence of a base.

An economic, one-step method for the production of N-substituted aromatic hydroxylamines of formula (I)
R—N(OH)—C(═O)—(O)R.sub.1  (I),
with hydrogen, by catalytic hydration with possibly modified hydration catalysts in an aprotic solvent and in the presence of a halogen formic acid ester and in some cases in the presence of a base.

An economic, one-step method for the production of N-substituted aromatic hydroxylamines of formula (I)
R—N(OH)—C(═O)—(O)R.sub.1  (I),
with hydrogen, by catalytic hydration with possibly modified hydration catalysts in an aprotic solvent and in the presence of a halogen formic acid ester and in some cases in the presence of a base.

A synthesis method for a candesartan cilexetil intermediate represented by formula (II) is provided. The method includes (1) dissolving a compound represented by formula (IV) to an aprotic solvent to obtain a first mixed solution, and dissolving a phase transfer catalyst and an azidation reagent to water to obtain a second mixed solution; (2) dropping the first mixed solution to the second mixed solution for azidation reaction, and after the reaction is ended, standing and layering same to obtain an organic phase containing a compound represented by formula (V); (3) dropping the obtained organic phase containing the compound represented by formula (V) to tertiary butyl alcohol for rearrangement reaction, and after the reaction is ended, concentrating same to obtain a solid or oily material, then adding a crystallizing solvent to the obtained solid or oily material for recrystallization, and separating same to obtain a crystal.

A synthesis method for a candesartan cilexetil intermediate represented by formula (II) is provided. The method includes (1) dissolving a compound represented by formula (IV) to an aprotic solvent to obtain a first mixed solution, and dissolving a phase transfer catalyst and an azidation reagent to water to obtain a second mixed solution; (2) dropping the first mixed solution to the second mixed solution for azidation reaction, and after the reaction is ended, standing and layering same to obtain an organic phase containing a compound represented by formula (V); (3) dropping the obtained organic phase containing the compound represented by formula (V) to tertiary butyl alcohol for rearrangement reaction, and after the reaction is ended, concentrating same to obtain a solid or oily material, then adding a crystallizing solvent to the obtained solid or oily material for recrystallization, and separating same to obtain a crystal.

The present invention relates to the compound 2-ethyl-5,5-dimethyl-cyclohexanol, which can impart, modify and/or enhance one or more odours selected from the group consisting of minty, fresh tobacco leaf, cresol, horse and animalistic, mixtures comprising 2-ethyl-5,5-dimethyl-cyclohexanol, and a new method for producing the same, a fragrance composition comprising 2-ethyl-5,5-dimethyl-cyclohexanol, the use of 2-ethyl-5,5-dimethyl-cyclohexanol as a fragrance, particularly for imparting, modifying and/or enhancing one or more odours selected from the group consisting of minty, fresh tobacco leaf, cresol, horse and animalistic, a perfumed product comprising 2-ethyl-5,5-dimethyl-cyclohexanol, a method for perfuming such a product and a method for modifying an olfactory impression.

The present invention relates to the compound 2-ethyl-5,5-dimethyl-cyclohexanol, which can impart, modify and/or enhance one or more odours selected from the group consisting of minty, fresh tobacco leaf, cresol, horse and animalistic, mixtures comprising 2-ethyl-5,5-dimethyl-cyclohexanol, and a new method for producing the same, a fragrance composition comprising 2-ethyl-5,5-dimethyl-cyclohexanol, the use of 2-ethyl-5,5-dimethyl-cyclohexanol as a fragrance, particularly for imparting, modifying and/or enhancing one or more odours selected from the group consisting of minty, fresh tobacco leaf, cresol, horse and animalistic, a perfumed product comprising 2-ethyl-5,5-dimethyl-cyclohexanol, a method for perfuming such a product and a method for modifying an olfactory impression.

The present invention aims to provide a new method for producing an indole compound or a salt thereof, which has an ITK inhibitory action, and is useful for the prophylaxis or treatment of inflammatory disease. The present invention is a method for producing N-[2-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)-1H-indol-6-yl]-N-methyl-(2S)-2-(morpholin-4-yl)propanamide, which comprises a step of reacting ##STR00001##

The present invention aims to provide a new method for producing an indole compound or a salt thereof, which has an ITK inhibitory action, and is useful for the prophylaxis or treatment of inflammatory disease. The present invention is a method for producing N-[2-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)-1H-indol-6-yl]-N-methyl-(2S)-2-(morpholin-4-yl)propanamide, which comprises a step of reacting ##STR00001##

The present invention provides a method for producing a carbamate that includes a step (1) and a step (2) described below: (1) a step of producing a compound (A) having a urea linkage, using an organic primary amine having at least one primary amino group per molecule and at least one compound selected from among carbon dioxide and carbonic acid derivatives, at a temperature lower than the thermal dissociation temperature of the urea linkage; and (2) a step of reacting the compound (A) with a carbonate ester to produce a carbamate.