Claims
- 1. A process for preparing a triarylmethane derivative having the structural formula ##STR212## wherein each R.sub.1 and R.sub.2 represents at least one of hydrogen, halogen, nitro group, alkyl group, amino group, alkyl-, benzyl-, phenyl-, tolyl-, or pentylene-substituted amino group, hydroxyl group, alkyl-substituted hydroxyl group, thiohydroxyl group or alkyl-substituted thiohydroxyl group, each R.sub.3 and R.sub.4 represents hydrogen, cyano-, hydroxyl-, halogen-, methoxy-, ethoxy-, or ethoxycarbonyl-substituted or unsubstituted alkyl group, cycloalkyl group, alkyl-substituted or unsubstituted aralkyl group, aryl group, or unsaturated alkyl group, or one or both of R.sub.3 and R.sub.4 together with the adjacent nitrogen atom may form a morpholine ring, a pyrrolidine ring, a pyrazolidine ring, a piperidine ring, an imidazoline ring, a piperazine ring, or a pyrimidine ring, R.sub.5 represents at least one of hydrogen, halogen, alkyl group, nitro group, lower alkyl-substituted or unsubstituted amino group, lower alkyl-substituted or unsubstituted hydroxyl group, or lower alkyl-substituted or unsubstituted thiohydroxyl group, R.sub.6 represents at least one of hydrogen, halogen, lower alkyl group, lower alkoxyl group, amino group, lower alkylamino group, nitro group, phenyl group or phenoxy group, R.sub.7 represents hydrogen, alkyl group, aralkyl group or phenyl group, R.sub.8 represents an alkyl group or alkyl-, halogen-, or alkoxy-substituted or unsubstituted phenyl group which comprises oxidizing a triarylmethane derivative having the structural formula ##STR213## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are the same as described hereinbefore, said triarylmethane derivative having the structural formula (I) or (II) being obtained by the reaction of 3-phenylphthalide having the structural formula ##STR214## wherein R.sub.1 and R.sub.2 are the same as described hereinbefore with the aniline derivative having the structural formula ##STR215## wherein R.sub.3, R.sub.4 and R.sub.5 are the same as described hereinbefore, or with the indole derivative having the structural formula ##STR216## wherein R.sub.6, R.sub.7 and R.sub.8 are the same as described hereinbefore in the presence of a Friedel-Crafts type catalyst.
- 2. A process for preparing triarylmethane derivative as defined in claim 1, wherein said 3-phenylphthalide derivatives having the structural formula (V) has R.sub.2 at the 6 position.
- 3. A process for preparing triarylmethane derivative as defined in claim 2, wherein said R.sub.2 is at least one alkyl-, benzyl-, phenyl-, tolyl-, or pentylene-substituted amino group.
- 4. A process for preparing triarylmethane derivative as defined in claim 1, wherein said Friedel-Crafts type catalyst comprises at least one member selected from the group consisting of acidic halide Lewis acid catalysts, Br nsted acid catalysts, acidic oxide catalysts, metal alkyl Lewis acid catalysts and metal alkoxide Lewis acid catalysts.
- 5. A process for preparing triarylmethane derivative as defined in claim 4, wherein said Friedel-Crafts type catalyst comprises at least one member selected from the group consisting of acidic halide Lewis acid catalysts, Br nsted acid catalysts and acidic oxide catalysts.
- 6. A process for preparing triarylmethane derivative as defined in claim 1, wherein said Friedel-Crafts type catalyst is used in an equimolar amount with respect to said 3-phenylphthalide derivative or more.
- 7. A process for preparing triarylmethane derivative as defined in claim 1, wherein the reaction of said 3-phenylphthalide derivative with said aniline derivative or said indole derivative is carried out a temperature within the range of 0.degree. to 180.degree. C.
- 8. A process for preparing triarylmethane derivative as defined in claim 1, wherein said triarylmethane derivative having the general formula (I) or (II) is oxidized with use of an oxidizing agent.
- 9. A process for preparing triarylmethane derivative as defined in claim 8, wherein said oxidizing agent is used in an excess of a stoichiometric amount based on the amount of said triarylmethane derivative having the structural formula (I) or (II).
- 10. A process for preparing triarylmethane derivative as defined in claim 1, wherein the reaction of said 3-phenylphthalide derivative with said aniline derivative or said indole derivative to form said triarylmethane derivative having the structural formula (I) or (II) is immediately followed by and concurrently occurs with the oxidizing reaction to form said triarylmethane derivative having the structural formula (III) or (IV).
- 11. A process for preparing triarylmethane derivative as defined in claim 10, wherein said Friedel-Crafts type catalyst comprises at least one member selected from the group of FeCl.sub.3, FeBr.sub.3, AgNO.sub.3, CuCl.sub.2 or peracetic acid.
- 12. A process for preparing triarylmethane derivative as defined in claim 10, wherein said 3-phenylphthalide derivatives having the structural formula (V) has R.sub.2 at the 6 position.
- 13. A process for preparing triarylmethane derivative as defined in claim 12, wherein said R.sub.2 is at least one alkyl-, benzyl-, phenyl-, tolyl-, or pentylene-substituted amino group.
- 14. A process for preparing triarylmethane derivative as defined in claim 11, wherein said Friedel-Crafts type catalyst is used in an excess of the total amount of an equimolar amount with respect to said 3-phenylphthalide derivative and a stoichiometric amount based on the amount of said triarylmethane derivative having the structural formula (I) or (II).
- 15. A process for preparing triarylmethane derivative as defined in claim 10, wherein the reaction of said 3-phenylphthalide derivative with said aniline derivative or said indole derivative is carried out a temperature within the range of 0.degree. to 180.degree. C.
- 16. A process for preparing triarylmethane derivatives as defined in claim 1, wherein said triarylmethane derivatives having the structural formula (I) or (II) is oxidized in the presence of at least one oxidizing agent selected from the group consisting of manganese compounds, chromic acid compounds, lead compounds, copper compounds, cobalt compounds, cerium compounds, silver compounds, iron compounds, SeO.sub.2, RuO.sub.4, OsO.sub.4, inorganic peroxides, organic peroxides, halides, oxygen, ozone, ultraviolet rays, sulfoxides, amino acids and chloranil.
- 17. A process for preparing triarylmethane derivatives as defined in claim 10, wherein the oxidizing agent is selected from the group consisting of ferric chloride, potassium persulfate, chloranil, potassium permanganate, ferric sulfate, sodium hypochlorite, peracetic acid, silver nitrate, lead peroxide, cupric chloride, potassium dichromate and hydrogen peroxide.
- 18. A process for preparing triarylmethane derivatives as defined in claim 1, wherein said oxidation is with at least one oxidizing agent selected from the group consisting of permanganates, manganese dioxide, manganese (III) salts, chromic anhydride, chromic acid, perchromates, alkyl esters of chromic acid, chromyl chloride, lead compounds, copper compounds, cobalt (III) compounds, cerium (IV) compounds, NaBiO.sub.3, bismuthoxide, bismuthacetate, silver (I) compounds, iron (III) compounds, SeO.sub.2, RuO.sub.4, OsO.sub.4, hydrogen peroxide, persulfuric acid, persulfuric acid salts, peroxides of aliphatic or carboxylic acid, hypochlorites, chlorates, hypobromites, bromates, oxygen, ozone, dimethyl sulfoxides, amine oxides and chloranil.
- 19. A process for preparing triarylmethane derivatives as defined in claim 1, wherein said oxidation is with at least one oxidizing agent selected from the group consisting of permanganates, manganese dioxide, manganese (III) salts, manganese acetate, chromic anhydride, chromic acid, perchromates, chromyl chloride, PbO, PbO.sub.2, Pb(OCOCH.sub.3).sub.4, CuO, Cu(OH).sub.2, CuSO.sub.4, Cu(OCOCH.sub.3).sub.2, CuCl.sub.2, CuBr.sub.2, Co.sub.2 (SO.sub.4).sub.3, Co.sub.3 O.sub.4, CeO.sub.2, Ce(SO.sub.4).sub.2, Ce(SO.sub.4).sub.3, NaBiO.sub.3, BiO, Bi(OCOCH.sub.3).sub.2, Ag.sub.2 O, AgOCOCH.sub.3, AgNo.sub.3, FeCl.sub.3, Fe.sub.2 (SO.sub.4).sub.3, potassium ferricyanate, SeO.sub.2, RuO.sub.4, OsO.sub.4, hydrogen peroxide, persulfuric acid, persulfuric acid salts, performic acid, peracetic acid, perpropionic acid, perbutyric acid, perbenzoic acid, monoperphthalic acid, monoperterephthalic acid, monopersuccinic acid, trifluoroperacetic acid, hypochlorites, chlorates, hypobromites, bromates, oxygen, ozone, sulfoxides, amine oxides and chloranil.
- 20. A process for preparing a triarylmethane derivative having the structural formula: ##STR217## wherein each R.sub.1 and R.sub.2 represent at least one of hydrogen, halogen, a nitro group, an alkyl group, an amino group, an alkyl-, benzyl-, phenyl-, tolyl-, or pentylene-substituted amino group, a hydroxyl group, an alkyl-substituted hydroxyl group, a thiohydroxyl group or an alkyl-substituted thiohydroxyl group, R.sub.6 represents at least one of hydrogen, halogen, lower alkyl group, lower alkoxyl group, amino group, lower alkylamino group, nitro group, phenyl group or phenoxy group, R.sub.7 represents hydrogen, alkyl group, aralkyl group or phenyl group, R.sub.8 represents an alkyl group or alkyl-, halogen-, or alkoxy-substituted or unsubstituted phenyl group which comprises reacting a 3-phenylphthalide derivative having the structural formula: ##STR218## wherein R.sub.1 and R.sub.2 are the same as described hereinabove, with an indole derivative having the structural formula: ##STR219## wherein R.sub.6, R.sub.7 and R.sub.8 are the same as hereinabove defined, in the presence of a Friedel-Crafts type catalyst.
- 21. A process for preparing a triarylmethane derivative having the structural formula: ##STR220## wherein each R.sub.1 and R.sub.2 represents at least one of hydrogen, halogen, nitro group, alkyl group, amino group, alkyl-, benzyl-, phenyl-, tolyl-, or pentylene-substituted amino group, hydroxyl group, alkyl-substituted hydroxyl group, thiohydroxyl group or alkyl-substituted thiohydroxyl group, R.sub.6 represents at least one of hydrogen, halogen, lower alkyl group, lower alkoxyl group, amino group, lower alkylamino group, nitro group, phenyl group or phenoxy group, R.sub.7 represents hydrogen, alkyl group, benzyl group or phenyl group, R.sub.8 represents an alkyl group or alkyl-, halogen-, or alkoxy-substituted or unsubstituted phenyl group which comprises oxidizing a triarylmethane derivative having the structural formula ##STR221## wherein R.sub.1, R.sub.2, R.sub.6, R.sub.7 and R.sub.8 are the same as described hereinbefore with an oxidizing agent, said triarylmethane derivative having the structural formula (II) being obtained by the reaction of 3-phenylphthalide having the structural formula ##STR222## wherein R.sub.1 and R.sub.2 are the same as the described hereinbefore with the indole derivative having the structural formula ##STR223## wherein R.sub.6, R.sub.7 and R.sub.8 are the same as described hereinbefore in the presence of a Friedel-Crafts type catalyst, said oxidizing agent being at least one selected from the group consisting of permanganates, manganese dioxide, manganese (III) salts, chromic anhydride, chromic acid, perchromates, alkyl esters of chromic acid, chromyl chloride, lead compounds, copper compounds, cobalt (III) compounds, cerium (IV) compounds, NaBiO.sub.3, bismuthoxide, bismuthacetate, silver (I) compounds, iron (III) compounds, SeO.sub.2, RuO.sub.4, OsO.sub.4, hydrogen peroxide, persulfuric acid, persulfuric acid salts, peroxides of aliphatic or carboxylic acid, hypochlorites, chlorates, hypobromites, bromates, oxygen, ozone, dimethyl sulfoxides, amine oxides and chloranil.
- 22. A process for preparing a triarylmethane derivative as claimed in claim 18 wherein each R.sub.3 and R.sub.4 represents hydrogen, an alkyl group, a benzyl group, or a phenyl group.
- 23. A process for preparing a triarylmethane derivative having the structural formula ##STR224## wherein each R.sub.1 and R.sub.2 represents at least one of hydrogen, halogen, nitro group, alkyl group, amino group, alkyl-, benzyl-, phenyl-, tolyl-, or pentylene-substituted amino group, hydroxyl group, alkyl-substituted hydroxyl group, thiohydroxyl group or alkyl-substituted thio-hydroxyl group, each R.sub.3 and R.sub.4 represents hydrogen, cyano-, hydroxyl-, halogen-, methoxy-, ethyoxy-, or ethoxycarbonyl-substituted or unsubstituted alkyl group, cycloalkyl group, alkyl-substituted or unsubstituted aralkyl group, aryl group, or unsaturated alkyl group, or one or both of R.sub.3 and R.sub.4 together with the adjacent nitrogen atom may form a morpholine ring, a pyrrolidine ring, a pyrazolidine ring, a piperidine ring, an imidazoline ring, a piperazine ring, or a pyrimidine ring, R.sub.5 represents at least one of hydrogen, halogen, alkyl group, nitro group, lower alkyl-substituted or unsubstituted amino group, lower alkyl-substituted or unsubstituted hydroxyl group, or lower alkyl-substituted or unsubstituted thiohydroxyl group, R.sub.6 represents at least one of hydrogen, halogen, lower alkyl group, lower alkoxyl group, amino group, lower alkyl-amino group, nitro group, phenyl group or phenoxy group, R.sub.7 represents hydrogen, alkyl group, aralkyl group or phenyl group, R.sub.8 represents an alkyl group or alkyl-, halogen-, or alkoxy-substituted or unsubstituted phenyl group which comprises oxidizing a triarylmethane derivative having the structural formula ##STR225## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are the same as described hereinbefore, said triarylmethane derivative having the structural formula (I) or (II) being obtained by the reaction of 3-phenylphthalide having the structural formula ##STR226## wherein R.sub.1 and R.sub.2 are the same as described hereinbefore with the aniline derivative having the structural formula ##STR227## wherein R.sub.3, R.sub.4 and R.sub.5 are the same as described hereinbefore, or with the indole derivative having the structural formula ##STR228## wherein R.sub.6, R.sub.7 and R.sub.8 are the same as described hereinbefore in the presence of a Friedel-Crafts type catalyst.
Priority Claims (1)
| Number |
Date |
Country |
Kind |
| 50-82898 |
Jul 1975 |
JPX |
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Parent Case Info
This is a division of application Ser. No. 699,584 filed June 24, 1976 now U.S. Pat. No. 4,045,458.
US Referenced Citations (7)
Divisions (1)
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Number |
Date |
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| Parent |
699584 |
Jun 1976 |
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Patent Grant
4439610
