Provided are a water-soluble naphthoquinone derivative composition and a method for preparing the same, a water-soluble composition for controlling harmful algae, a method of controlling large-scale harmful algae, and an automated system for artificial intelligence monitoring, removal, and prevention of large-scale harmful algae. According to one embodiment, a method of preparing a water-soluble naphthoquinone derivative composition includes reacting a 1,4-naphthoquinone compound with N,N-diethylethylenediamine to obtain an intermediate product of [Chemical Formula 2]; and reacting an intermediate product of [Chemical Formula 2] with hydrochloric acid to obtain a compound of [Chemical Formula 1]. In addition, the water-soluble naphthoquinone derivative composition represented by the following [Chemical Formula 1] is proposed. In addition, a water-soluble composition is proposed for controlling harmful algae, a method for controlling large-scale harmful algae using the water-soluble composition for controlling harmful algae, and an automated system for artificial intelligence monitoring, removal, and prevention of large-scale harmful algae.

The present invention is a method of making 1,4,5,8-tetrakis(R-phenylamino)anthracene-9,10-dione (where R is H or a hydrocarbyl group) comprising the step of contacting 1,4,5,8-tetrachloroanthraquinone with a mixture of R-anilines comprising at least two different R groups, under conditions to produce 1,4,5,8-tetrakis(R-phenylamino)anthracene-9,10-dione. The present disclosure also provides a reaction mixture of 1,4,5,8-tetrakis(R-phenylamino)anthracene-9,10-dione characterized by having the R groups on at least 75% of the 1,4,5,8-tetrakis(R-amino)anthracene-9,10-dione molecules in the mixture be comprised of 2 or more different R groups. The present disclosure also provides a method of improving the solubility of 1,4,5,8-tetrakis(R-phenylamino)anthracene-9,10-dione in aromatic hydrocarbons distilled from crude oil, comprising selecting a mixture of 1,4,5,8-tetrakis(R-phenylamino)anthracene-9,10-diones which are characterized by having at least 75% of the 1,4,5,8-tetrakis(R-phenylamino)anthracene-9,10-dione molecules in the mixture comprise two or more different R groups. The compounds of the present invention exhibit a suitable UV visible absorbance profile making them suitable for use as a fuel marker.

The present invention is a method of making 1,4,5,8-tetrakis(R-phenylamino)anthracene-9,10-dione (where R is H or a hydrocarbyl group) comprising the step of contacting 1,4,5,8-tetrachloroanthraquinone with a mixture of R-anilines comprising at least two different R groups, under conditions to produce 1,4,5,8-tetrakis(R-phenylamino)anthracene-9,10-dione. The present disclosure also provides a reaction mixture of 1,4,5,8-tetrakis(R-phenylamino)anthracene-9,10-dione characterized by having the R groups on at least 75% of the 1,4,5,8-tetrakis(R-amino)anthracene-9,10-dione molecules in the mixture be comprised of 2 or more different R groups. The present disclosure also provides a method of improving the solubility of 1,4,5,8-tetrakis(R-phenylamino)anthracene-9,10-dione in aromatic hydrocarbons distilled from crude oil, comprising selecting a mixture of 1,4,5,8-tetrakis(R-phenylamino)anthracene-9,10-diones which are characterized by having at least 75% of the 1,4,5,8-tetrakis(R-phenylamino)anthracene-9,10-dione molecules in the mixture comprise two or more different R groups. The compounds of the present invention exhibit a suitable UV visible absorbance profile making them suitable for use as a fuel marker.

The invention provides a method for synthesizing a compound of formula ##STR00001##
wherein each R independently represents an optionally substituted aryl, heteroaryl, alkyl, perfluoroalkyl, cycloalkyl, alkoxy, aryloxy, acyl, carboxyl, hydroxyl, halogen, amino, nitro, cyano, sulfo or sulfhydryl group, in ortho, meta or para position to the cycloalkylamine moiety; R.sup.1 and R.sup.2 each independently represents a hydrogen atom, a lower alkyl group or a cycloalkyl group; R.sup.3 represents a hydrogen group, substituted aryl, heteroaryl, alkyl, perfluoroalkyl, cycloalkyl, alkoxy, aryloxy group; Y represents an oxygen atom, a sulfur atom, a NH group, a NR.sup.4 group or a CH.sub.2 group;
R.sup.4 represents a hydrogen atom or an alkyl, aryl or a heteroaryl group; and n and m each independently represents an integer from 1 to 5; or a pharmaceutically acceptable salt thereof; or a precursor thereof; wherein the method comprises one or more of the following steps: (a) reacting a compound of formula (II) ##STR00002##
wherein R, R.sup.3, Y, n and m are as defined above in relation to the compound of formula (I) with an oxygenating agent, a first additive and a second additive in a solvent in a fluidic network or in a batch process under thermal and/or photochemical conditions to form a compound of formula (III): ##STR00003##
wherein R, R.sup.3, Y, n and m are as defined above in relation to the compound of formula (I), (b) reacting a compound of formula (III) with a nitrogen containing nucleophile in the presence of a third additive and/or a solvent in the fluidic network or in a batch process under thermal conditions to form a compound of formula (IV): ##STR00004##
wherein R, R.sub.1, R.sub.2, R.sub.3, Y, n and m are as defined above in relation to the compound of formula (I); and/or
(c) reacting a compound of formula (IV) in a fluidic network or in a batch process, optionally in the presence of a fourth additive, under thermal conditions to form a compound of formula (I); wherein one or more of steps (a), (b) and/or (c) is carried out in a fluidic network that comprises micro- and/or meso-channels having an internal dimension of from 100 μm to 2000 μm.

The invention provides a method for synthesizing a compound of formula ##STR00001##
wherein each R independently represents an optionally substituted aryl, heteroaryl, alkyl, perfluoroalkyl, cycloalkyl, alkoxy, aryloxy, acyl, carboxyl, hydroxyl, halogen, amino, nitro, cyano, sulfo or sulfhydryl group, in ortho, meta or para position to the cycloalkylamine moiety; R.sup.1 and R.sup.2 each independently represents a hydrogen atom, a lower alkyl group or a cycloalkyl group; R.sup.3 represents a hydrogen group, substituted aryl, heteroaryl, alkyl, perfluoroalkyl, cycloalkyl, alkoxy, aryloxy group; Y represents an oxygen atom, a sulfur atom, a NH group, a NR.sup.4 group or a CH.sub.2 group;
R.sup.4 represents a hydrogen atom or an alkyl, aryl or a heteroaryl group; and n and m each independently represents an integer from 1 to 5; or a pharmaceutically acceptable salt thereof; or a precursor thereof; wherein the method comprises one or more of the following steps: (a) reacting a compound of formula (II) ##STR00002##
wherein R, R.sup.3, Y, n and m are as defined above in relation to the compound of formula (I) with an oxygenating agent, a first additive and a second additive in a solvent in a fluidic network or in a batch process under thermal and/or photochemical conditions to form a compound of formula (III): ##STR00003##
wherein R, R.sup.3, Y, n and m are as defined above in relation to the compound of formula (I), (b) reacting a compound of formula (III) with a nitrogen containing nucleophile in the presence of a third additive and/or a solvent in the fluidic network or in a batch process under thermal conditions to form a compound of formula (IV): ##STR00004##
wherein R, R.sub.1, R.sub.2, R.sub.3, Y, n and m are as defined above in relation to the compound of formula (I); and/or
(c) reacting a compound of formula (IV) in a fluidic network or in a batch process, optionally in the presence of a fourth additive, under thermal conditions to form a compound of formula (I); wherein one or more of steps (a), (b) and/or (c) is carried out in a fluidic network that comprises micro- and/or meso-channels having an internal dimension of from 100 μm to 2000 μm.

A process for the preparation of (2R,6R)-hydroxynorketamine is provided. The process requires no chromatography purification and affords the (2R,6R)-hydroxynorketamine in eight steps with a 26% overall yield and greater than 97% purity.

A process for the preparation of (2R,6R)-hydroxynorketamine is provided. The process requires no chromatography purification and affords the (2R,6R)-hydroxynorketamine in eight steps with a 26% overall yield and greater than 97% purity.

A process for the preparation of (2R,6R)-hydroxynorketamine is provided. The process requires no chromatography purification and affords the (2R,6R)-hydroxynorketamine in eight steps with a 26% overall yield and greater than 97% purity.

The present invention disclosed a process for the synthesis of compound of formula (Z) or a salt thereof,

##STR00001##

wherein, R, R.sup.1, R.sup.2, R.sup.3 and R.sup.10 are as defined in the detailed description. The process further comprises the synthesis of an anthranilic diamide compound of formula (I).

The present invention disclosed a process for the synthesis of compound of formula (Z) or a salt thereof,

##STR00001##

wherein, R, R.sup.1, R.sup.2, R.sup.3 and R.sup.10 are as defined in the detailed description. The process further comprises the synthesis of an anthranilic diamide compound of formula (I).