GB461185A - Improved manufacture of bases derived from ª‡-aminopyridine - Google Patents
Improved manufacture of bases derived from ª‡-aminopyridineInfo
- Publication number
- GB461185A GB461185A GB2212535A GB2212535A GB461185A GB 461185 A GB461185 A GB 461185A GB 2212535 A GB2212535 A GB 2212535A GB 2212535 A GB2212535 A GB 2212535A GB 461185 A GB461185 A GB 461185A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dipyridylamine
- treated
- aminopyridine
- nitro
- amino
- 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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Abstract
Nitro derivatives of pyridine compounds substituted in the 2-position with a group --NHR, where R is a non-reduced homocyclic or heterocyclic radicle, are treated with hydrogen under pressure in the presence of a hydrogenation catalyst, whereby reduction of the nitro group or groups is effected and amino compounds are obtained. In the examples, (1) 5-nitro-2 : 2<1>-dipyridylamine is treated with hydrogen at 50 DEG C. and 10--15 atm. pressure in the presence of platinic oxide, or of palladium on charcoal; the base obtained is isolated by way of its hydrochloride; (2) a mixture of 3 : 3<1>- and 3 : 5<1>-dinitro-2 : 2<1>-dipyridylamine, obtained by nitrating 2 : 2<1>-dipyridylamine, is reduced as in example 1; the hydrochlorides of the products are separable by virtue of their different solubilities; (3) 2<1> : 4<1>-dinitrophenyl-2-aminopyridine (from 2-aminopyridine and 1-chloro-2 : 4-dinitrobenzene) is treated with hydrogen at 50 DEG C. and 3-5 atm. pressure in the presence of a catalyst specified in example 1; the condensation product of 5-amino-2 : 2<1>-dipyridylamine with 1-chloro-2 : 4-dinitrobenzene may be similarly treated. The provisional Specification refers to (1) the production of 2 : 2<1>-dipyridylamine by heating 2-aminopyridine with its hydrochloride for 6-7 hours; (2) the production of 5-nitro-2 : 2<1>-dipyridylamine by nitrating 2 : 2<1>-dipyridylamine and by condensing 2-aminopyridine with 2-chloro-5-nitropyridine; (3) the production of 5 : 5<1>-dinitro-2 : 2<1>-dipyridylamine by condensing 2-chloro-5-nitropyridine with 2-amino-5-nitropyridine; (4) the conversion of 5-amino-2 : 2<1>-dipyridylamine into its acetyl, phenylcarbamino and xenylcarbamino derivatives; (5) the production of 5 : 5<1>-diamino-2 : 2<1>-dipyridylamine by reducing the corresponding dinitro compound.ALSO:Nitro derivatives of pyridine compounds substituted in the 2-position with a group --NHR, where R is a non-reduced homocyclic or heterocyclic radicle, are treated with hydrogen under pressure in the presence of a hydrogenation catalyst, whereby reduction of the nitro group or groups is effected and amino compounds are obtained. In the examples, (1) 5-nitro-2 : 2<1>-dipyridylamine is treated with hydrogen at 50 DEG C. and 10--15 atm. pressure in the presence of platinic oxide, or of palladium on charcoal; (2) a mixture of 3 : 3<1>-and 3 : 5<1>-dinitro-2 : 2<1>-dipyridylamine is reduced as in example 1; the hydrochloride of the products are separable by virtue of their different solubilities; (3) 2<1> : 4<1>-dinitrophenyl2-aminopyridine is treated with hydrogen at 50 DEG C. and 3--5 atm. pressure in the presence of a catalyst specified in example 1; the condensation product of 5-amino-2 : 2<1>-dipyridylamine with 1-chloro-2 : 4-dinitro benzene may be similarly treated. The Provisional Specification refers to the production of 5 : 5<1>-diamino-2 : 2<1>-dipyridylamine by reducing the corresponding dinitro compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2212535A GB461185A (en) | 1935-08-06 | 1935-08-06 | Improved manufacture of bases derived from ª‡-aminopyridine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2212535A GB461185A (en) | 1935-08-06 | 1935-08-06 | Improved manufacture of bases derived from ª‡-aminopyridine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB461185A true GB461185A (en) | 1937-02-08 |
Family
ID=10174299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2212535A Expired GB461185A (en) | 1935-08-06 | 1935-08-06 | Improved manufacture of bases derived from ª‡-aminopyridine |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB461185A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3647351A (en) * | 1963-04-19 | 1972-03-07 | Schwarzkopf Gmbh Hans | Pyridine dyestuff intermediates in a hair dyeing composition and method |
| CN106748834A (en) * | 2017-01-12 | 2017-05-31 | 陕西师范大学 | A kind of method that the bipyridyl of 4,4 dimethoxy 2,2 silver catalytic hydrogenation aromatic nitro compound synthesizes arylamine |
-
1935
- 1935-08-06 GB GB2212535A patent/GB461185A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3647351A (en) * | 1963-04-19 | 1972-03-07 | Schwarzkopf Gmbh Hans | Pyridine dyestuff intermediates in a hair dyeing composition and method |
| CN106748834A (en) * | 2017-01-12 | 2017-05-31 | 陕西师范大学 | A kind of method that the bipyridyl of 4,4 dimethoxy 2,2 silver catalytic hydrogenation aromatic nitro compound synthesizes arylamine |
| CN106748834B (en) * | 2017-01-12 | 2018-05-08 | 陕西师范大学 | A kind of method of 4,4- dimethoxys -2,2- bipyridyl silver catalytic hydrogenations aromatic nitro compound synthesis arylamine |
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