GB899014A - New derivatives of phenoxazine and processes for their production - Google Patents
New derivatives of phenoxazine and processes for their productionInfo
- Publication number
- GB899014A GB899014A GB900260A GB900260A GB899014A GB 899014 A GB899014 A GB 899014A GB 900260 A GB900260 A GB 900260A GB 900260 A GB900260 A GB 900260A GB 899014 A GB899014 A GB 899014A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- nr3r4
- phenoxazine
- carbon atoms
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B19/00—Oxazine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention comprises compounds of the formula <FORM:0899014/IV (b)/1> (wherein R1 and R2 are alkyl groups of 2 to 5 carbon atoms and R3 and R4 are alkyl groups of 2 to 5 carbon atoms or together with the adjacent-nitrogen atom form a piperidine or pyrrolidine ring) and acid addition salts thereof; and their preparation by reducing a 2-nitroso-5-NR3R4-phenol to the corresponding 2-amino-5-NR3R4-phenol, condensing this with a 1 : 3-dihalogeno - 4 : 6 - dinitrobenzene to form a 3 - halogeno - 4 : 6- dinitro - 21 - hydroxy - 4 1 - NR3R4-diphenylamine, aminating this to yield a 3 - NHR1 - 4 : 6 - dinitro - 21 - hydroxy - 41 - NR3R4-diphenylamine, reducing and cyclizing this to form a 2-amino-2-NHR1-7-NR3R4-phenoxazine, oxidising this to a compound of the formula <FORM:0899014/IV (b)/2> and alkylating this to give the desired product. The phenoxazine is advantageously oxidized in solution by bubbling air therethrough and the final alkylation may be achieved either by aminolysis, e.g. treating a salt of the phenoxazine with an excess of the appropriate amine R2NH2, or, where R2 is a branched chain alkyl group of 3 to 5 carbon atoms, by condensing the phenoxazine with a ketone r-CO-r1 (r and r1 being methyl or ethyl groups) to give a compound of the formula <FORM:0899014/IV (b)/3> and cleaving the imidazole ring of this by hydrogenation. The invention also comprises an alternative process for the preparation of the compounds of the invention wherein 6-nitro-benz-imidazole is alkylated to obtain 6-nitro-N1-alkylbenzimidazole, this, preferably as the sodium or potassium derivative, is reacted with alkyl halide to give a compound of the formula <FORM:0899014/IV (b)/4> (X being a halogen atom), this is treated with a strong alkali to yield a 1-NHR1-2-NHR2-4-nitro-benzene, this is reduced to a 1-NHR1-2-NHR2-4-amino-benzene and this is condensed with a 2-nitroso-5-NR3R4-phenol to yield the desired product. Examples are given. N - (3 - hydroxy - 4 - nitroso - phenyl) - piperidine hydrochloride is prepared by nitrosation of N-(3-hydroxyphenyl)-piperidine.ALSO:The invention comprises compounds of the formula <FORM:0899014/IV (c)/1> (wherein R1 and R2 are alkyl groups of 2 to 5 carbon atoms and R3 and R4 are alkyl groups of 2 to 5 carbon atoms or together with the adjacent nitrogen atom form a piperidine or pyrrolidine ring) and acid-addition salts thereof; and their preparation by a process the last two stages of which comprise oxidizing a compound of the formula <FORM:0899014/IV (c)/2> to give a compound of the formula <FORM:0899014/IV (c)/3> and alkylating this either directly by aminolysis with the appropriate amine R2NH2 or, where R2 is a branched alkyl group of 3 to 5 carbon atoms, by condensing the phenoxazine with a ketone r-CO-r1 (r and r1 being methyl or ethyl) to give a compound of the formula <FORM:0899014/IV (c)/4> and cleaving this by hydrogenation. Alternatively, they may be prepared by condensing an appropriate 1, 2 - di (monoalkylamino) - 4 - amino - benzene with an appropriate 2-nitroso-5-dialkylamino-phenol. Examples are given.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB900260A GB899014A (en) | 1960-03-14 | 1960-03-14 | New derivatives of phenoxazine and processes for their production |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB900260A GB899014A (en) | 1960-03-14 | 1960-03-14 | New derivatives of phenoxazine and processes for their production |
Publications (1)
Publication Number | Publication Date |
---|---|
GB899014A true GB899014A (en) | 1962-06-20 |
Family
ID=9863468
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB900260A Expired GB899014A (en) | 1960-03-14 | 1960-03-14 | New derivatives of phenoxazine and processes for their production |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB899014A (en) |
-
1960
- 1960-03-14 GB GB900260A patent/GB899014A/en not_active Expired
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