Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Patent
1995-03-10
1997-06-17
Raymond, Richard L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
564393, 564443, C07C21300, C07C21306
Patent
active
056399154
DESCRIPTION:
BRIEF SUMMARY
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a 371 of PCT/JP93/01296 filed 10 Sep. 1993.
TECHNICAL FIELD
This invention relates to a process for producing an aniline derivative of the general formula (3): ##STR1## (where X.sup.1 and X.sup.2 represent a halogen atom and R represents an optionally substituted cycloalkyl group having 3-12 carbon atoms or an optionally substituted alkynyl group having 3-6 carbon atoms) by reacting a halogen-substituted aminophenol derivative of the general formula (1): ##STR2## with an alkylating agent of the general formula (2): metal hydroxide and an organic solvent in the presence of a phase transfer catalyst or in an organic solvent in the presence of an alkali metal carbonate.
The invention also relates to a process for producing an aniline derivative of the general formula (3): ##STR3## (where X.sup.1 and X.sup.2 represent a halogen atom and R represents an optionally substituted cycloalkyl group having 3-12 carbon atoms or an optionally substituted alkynyl group having 3-6 carbon atoms) by reacting a bis(amino-substituted phenyl)carbonate derivative of the general formula (4): ##STR4## with an alkylating agent of the general formula (2): metal hydroxide and an organic solvent in the presence of a phase transfer catalyst.
More specifically, this invention relates to processes for the production of intermediates for the manufacture of oxazolidinedione and tetrahydrophthalimide, as well as tetrahydroindazole derivatives which are useful as active ingredients of herbicides as described in Japanese Patent Public Disclosure No. Sho. 62-167713 or Japanese Patent Public Disclosure Nos. Hei. 4-145071 and Hei. 4-164067.
BACKGROUND ART
The production of aniline derivatives of the general formula (3) from halogen-substituted aminophenol derivatives of the general formula (1) usually starts with aminophenol derivatives in which the amino group suspected of doing harm to the reaction is protected with a suitable protective group and comprises the steps of alkylating the starting material on the oxygen atom in the presence of a base and thereafter removing the protective group. For instance, as exemplified by Reaction Scheme (I) given below, phenol (5) having the amino group protected as a carbamate group is alkylated and the ester is then hydrolyzed under basic conditions to produce an aniline derivative (see, for example, Reference Examples in Japanese Patent Public Disclosure Nos. Hei. 4-145071 and Hei. 4-164067) (see under Reference Examples 1 and 2 to be described later in this specification): ##STR5##
The production of aniline derivatives of the general formula (3) from bis(amino-substituted phenyl)carbonate derivatives of the general formula (4) usually starts with aminophenol derivatives that are prepared by first protecting with a suitable protective group the amino group suspected of doing harm to the reaction and by then hydrolyzing only the carbonate bond without impairing the protective group and the production process comprises the steps of alkylating the starting material on the oxygen atom in the presence of a base and thereafter removing the protective group. For instance, as exemplified by Reaction Scheme (II) given below, bis(5-alkoxycarbonyl-amino-2-chloro-4-fluorophenyl)carbonate (8) having the amino group protected as an alkyl carbamate group is hydrolyzed selectively to a phenol derivative (9), then alkylated and, thereafter, the carbamate group is hydrolyzed under basic conditions to produce an aniline derivative (3) (see, for example, Japanese Patent Public Disclosure No. Hei 5-17411 or Hei. 5-43525): ##STR6##
Thus, the prior art methods described above require additional steps for introducing and removing the amino protective group and this is disadvantageous from an economic viewpoint since not only is the reaction process extended but it is also necessary to use auxiliary materials as appropriate for the respective steps.
DISCLOSURE OF INVENTION
The present inventors conducted intensive studies to develop an industrially more advant
REFERENCES:
patent: 4484941 (1984-11-01), Nagano et al.
patent: 4818272 (1989-04-01), Hirai et al.
patent: 5118849 (1992-06-01), Schallner et al.
Aizawa Kiyomi
Ejiri Emiko
Hirai Kenji
Yano Tomoyuki
Kaken Pharmaceutical Co. Ltd.
Raymond Richard L.
Sagami Chemical Research Center
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