Described herein are novel reduction reactions. Compounds prepared by the methods disclosed herein are useful for preparation of certain anthranilamide compounds that are of interest as insecticides, such as, for example, the insecticides chlorantraniliprole and cyantraniliprole.

The invention provides a method for producing a dichloro addition product of an aliphatic olefin by photocatalysis under visible light. The method includes reacting an aliphatic olefin as a substrate with hydrochloric acid as a chlorine source in an organic solvent under visible light irradiation in the presence of copper chloride with visible light absorption ability as a catalyst, to obtain the dichloro addition product of the aliphatic olefin, wherein the reaction is carried out under an oxygen-containing atmosphere, the aliphatic olefin comprises a carbon-carbon double bond and a C9-C15 aliphatic chain connected to the carbon-carbon double bond by a covalent bond. In the invention, visible light is used to provide the energy and a transition metal chloride with visible light absorption ability is used to undergo light-induced electron transfer from chloride with a reaction substrate, thereby initiating an addition reaction to obtain a dichloro addition product.

The invention provides a method for producing a dichloro addition product of an aliphatic olefin by photocatalysis under visible light. The method includes reacting an aliphatic olefin as a substrate with hydrochloric acid as a chlorine source in an organic solvent under visible light irradiation in the presence of copper chloride with visible light absorption ability as a catalyst, to obtain the dichloro addition product of the aliphatic olefin, wherein the reaction is carried out under an oxygen-containing atmosphere, the aliphatic olefin comprises a carbon-carbon double bond and a C9-C15 aliphatic chain connected to the carbon-carbon double bond by a covalent bond. In the invention, visible light is used to provide the energy and a transition metal chloride with visible light absorption ability is used to undergo light-induced electron transfer from chloride with a reaction substrate, thereby initiating an addition reaction to obtain a dichloro addition product.

The present invention relates inter alia to a compound of formula (I) wherein R.sub.1, R.sub.2 and R.sub.3, are as defined in the specification and to compositions comprising the same and to the use of the compounds and to compositions of the compounds in treatment, for example in the treatment of fibrotic diseases or interstitial lung diseases, in particular idiopathic pulmonary fibrosis.

It is an object of the present invention to provide an excellent method for producing an excellent therapeutic agent. The solution of the present invention is as shown in the following scheme: ##STR00001##
wherein R.sup.1 represents a C1-C6 alkyl group, R.sup.2 represents a C1-C6 alkyl group, and R.sup.3 represents a C1-C6 alkyl group.

It is an object of the present invention to provide an excellent method for producing an excellent therapeutic agent. The solution of the present invention is as shown in the following scheme: ##STR00001##
wherein R.sup.1 represents a C1-C6 alkyl group, R.sup.2 represents a C1-C6 alkyl group, and R.sup.3 represents a C1-C6 alkyl group.

A process for preparing substituted biphenyls of the formula (I) which comprises reacting a compound of the formula (II) in the presence of a base and of a palladium catalyst, with an organoboron compound of the formula (IV).

##STR00001##

A process for preparing substituted biphenyls of the formula (I) which comprises reacting a compound of the formula (II) in the presence of a base and of a palladium catalyst, with an organoboron compound of the formula (IV).

##STR00001##

A method for preparing 3-methyl-2-nitrobenzoic acid is disclosed wherein 1,3-dimethyl-2-nitrobenzene is combined with an oxidation catalayst in the presence of an oxygen source and an initiator, provided that less than 99% of the 1,3-dimethyl-2-nitrobenzene is oxidized. A method for preparing compounds of Formula 7 and Formula 11 is also disclosed wherein the method is characterized by using 3-methyl-2-nitrobenzoic acid as prepared by the method disclosed above ##STR00001## wherein R.sup.1 is C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.6 cycloalkyl or C.sub.4-C.sub.7 alkylcycloalkyl.

A method for preparing 3-methyl-2-nitrobenzoic acid is disclosed wherein 1,3-dimethyl-2-nitrobenzene is combined with an oxidation catalayst in the presence of an oxygen source and an initiator, provided that less than 99% of the 1,3-dimethyl-2-nitrobenzene is oxidized. A method for preparing compounds of Formula 7 and Formula 11 is also disclosed wherein the method is characterized by using 3-methyl-2-nitrobenzoic acid as prepared by the method disclosed above ##STR00001## wherein R.sup.1 is C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.6 cycloalkyl or C.sub.4-C.sub.7 alkylcycloalkyl.