GB519660A - Improvements in the manufacture of heterocyclic compounds of the diazaline series - Google Patents
Improvements in the manufacture of heterocyclic compounds of the diazaline seriesInfo
- Publication number
- GB519660A GB519660A GB2818538A GB2818538A GB519660A GB 519660 A GB519660 A GB 519660A GB 2818538 A GB2818538 A GB 2818538A GB 2818538 A GB2818538 A GB 2818538A GB 519660 A GB519660 A GB 519660A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diazaline
- benz
- prepared
- hydrogen
- nitro
- 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
519,660. Diazalines. MORGAN, Sir G. T. and STEWART, J. Sept. 28, 1938, No. 28185. [Class 2 (iii)] Mono - nitro - 1:3 - diazalines are prepared by heating a dinitro-secondary amine of the general formula in a high boiling point medium' until nitrous fumes are evolved. ' The parent materials may conveniently be prepared by the method' described in Specification 461,185. High boiling media specified as suitable for use according to the present 'invention include nitrobenzene naphthalene and diphenyl. In examples (1) N - 21:41 - dinitro - phenyl - 2 - amino pyridine prepared by condensing 1-chloro-2:4-dinitrobenzene and 2-aminopyridine is mixed with an equal weight of naphthalene and boiled under reflux in a bath of molten metal. The product on extraction with hydrochloric acid is 1:3 pyrido - 7 - nitro - 4:5 benz - 1:3 diazaline. Instead of naphthalene, diphenyl may be used as the high boiling medium. The mononitro diazaline prepared as above is reduced catalytically by hydrogen under an initial pressure of 5 atmospheres in the presence of platinic oxide to the corresponding monoaminodiazaline. Reduction as above but using hydrogen under an initial pressure of 32 atmospheres results in the formation of tetrahydro-1:2-pyrido-7-amino- 4:5 benz-1:3 diazaline. The primary monoaminodiazaline on diazotization with nitrosylsulphuric acid in the presence of phosphoric acid followed by treatment of the diazo solution with alcohol gives 1:2-pyrido-4:5 benz-1:3 diazaline ; (2) N-2<1>-4<1>-dinitrophenyl-2-aminoquinoline prepared by refluxing 2-aminoquinoline and 1-chloro-2:4-dinitrobenzene in nitrobenzene solution is heated at 340‹-360‹C. under a pressure of 20 mm. Oxides of nitrogen are evolved and 1.2-quinolo-1-nitro-4:5-benz 1:3-diazaline sublimes. This material on catalytic reduction at 70‹C. under hydrogen at a pressure of 31 atmospheres in the presence of platinum oxide is converted into the corresponding aminodiazaline. The amino group is exchanged for hydrogen by the diazo reaction as in example (1) to give 1:2-quinolo-4:5-benz- 1:3-diazaline ; (3) N - 2<1>:4<1>- dinitrophenyl - 1- amino-isoquinoline prepared by refluxing I- aminoisoquinoline and 1-chloro : 2:4-dinitrobenzene in xylene solution is heated as in example (2) to give 1:2 (2<1>:1<1>) isoquinolo-7- nitro-4:5- benz-1:3-diazaline. This compound on catalytic reduction as in example (2) gives the corresponding monoaminodiazaline. The amino group is exchanged for hydrogen by the diazo reaction as in example (1) to give 1:2 isoquinolo-4:5 benz-1:3-diazaline ; (4) N-2':4'- dinitro-1<1>-naphthyl-2-aminopyridine prepared by refluxing 2-aminopyridine and 1-chloro-2:4- dinitronaphthalene in xylene solution is refluxed in nitrobenzene solution to form 1:2-pyrido-7- nitro-8:9-benzo-4:5 benz-1:3 diazaline. This is catalytically reduced as in example (1) to the corresponding monoaminodiazaline under a pressure of 5 atmospheres. At 31 atmospheres pressure nuclear hydrogenation takes place with the formation of tetrahydromonoaminobenzobenzdiazoline. The amino group is further exchanged for hydrogen by the diazo reaction as in example (1) ; (5) N-2<1>-4<1>-dinitro- 1<1>-naphthyl-2-aminoquinoline prepared by refluxing 2-aminoquinoline and 1-chloro-2:4- dinitronaphthalene in xylene solution is boiled under reflux in a molten metal both with twice its weight of diphenyl to give 1:2-quinolo-7- nitro-8:9-benzo-4:5 benz-1:3 diazaline. This is catalytically reduced as in example (1) to the corresponding monoaminodiazaline. The amino group is exchanged for hydrogen by the diazo reaction as in example (1); (6) N-2<1>:4<1>- dinitro - 1<1> -naphthyl - 1 - aminoisoquinoline prepared by refluxing 1-aminoisoquinoline and 1-chloro 2:4 dinitronaphthalene in xylene solution is heated on a molten metal bath in a mixed solution of nitrobenzene and phenol to form the corresponding nitrobenzobenzdiazaline. This compound is reduced catalytically with hydrogen under a pressure of 70 atmospheres to the monoaminobenzobenzdiazaline. This amino group is then exchanged for hydrogen by the diazo reaction as in example (1). Specification 496,258, also is referred to.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2818538A GB519660A (en) | 1938-09-28 | 1938-09-28 | Improvements in the manufacture of heterocyclic compounds of the diazaline series |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2818538A GB519660A (en) | 1938-09-28 | 1938-09-28 | Improvements in the manufacture of heterocyclic compounds of the diazaline series |
Publications (1)
Publication Number | Publication Date |
---|---|
GB519660A true GB519660A (en) | 1940-04-02 |
Family
ID=10271631
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2818538A Expired GB519660A (en) | 1938-09-28 | 1938-09-28 | Improvements in the manufacture of heterocyclic compounds of the diazaline series |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB519660A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2303805A1 (en) * | 1975-03-11 | 1976-10-08 | Hoechst Ag | BENZIMIDAZO (1,2-A) QUINOLEINES AND THEIR PREPARATION |
US4003750A (en) * | 1973-05-03 | 1977-01-18 | Eastman Kodak Company | Silver halide emulsion containing photographic sensitizing dyes |
FR2364214A2 (en) * | 1976-09-09 | 1978-04-07 | Hoechst Ag | BENZIMIDAZO- (1,2-A) -QUINOLEINS AND THEIR PREPARATION |
-
1938
- 1938-09-28 GB GB2818538A patent/GB519660A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4003750A (en) * | 1973-05-03 | 1977-01-18 | Eastman Kodak Company | Silver halide emulsion containing photographic sensitizing dyes |
FR2303805A1 (en) * | 1975-03-11 | 1976-10-08 | Hoechst Ag | BENZIMIDAZO (1,2-A) QUINOLEINES AND THEIR PREPARATION |
FR2364214A2 (en) * | 1976-09-09 | 1978-04-07 | Hoechst Ag | BENZIMIDAZO- (1,2-A) -QUINOLEINS AND THEIR PREPARATION |
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