GB2073742A - 4-Amino-3,5-dicyano-pyridine Compounds - Google Patents

4-Amino-3,5-dicyano-pyridine Compounds Download PDF

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Publication number
GB2073742A
GB2073742A GB8107274A GB8107274A GB2073742A GB 2073742 A GB2073742 A GB 2073742A GB 8107274 A GB8107274 A GB 8107274A GB 8107274 A GB8107274 A GB 8107274A GB 2073742 A GB2073742 A GB 2073742A
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Prior art keywords
alkyl
pyridine
parts
amino
aryl
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GB8107274A
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Imperial Chemical Industries Ltd
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Imperial Chemical Industries Ltd
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Priority to GB8107274A priority Critical patent/GB2073742A/en
Publication of GB2073742A publication Critical patent/GB2073742A/en
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    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C07D213/85—Nitriles in position 3

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)

Abstract

Novel 4-amino-3,5-dicyano-6- methylpyridine and its 2-alky and 2- aryl derivatives are prepared by interacting diacetonitrile with malononitrile and an orthoester.

Description

SPECIFICATION Pyridine Derivatives This invention relates to pyridine derivatives and more particularly to 4-amino-3,5-dicyano-6methylpyridine and its 2-alkyl and 2-aryi derivatives.
Thus, in accordance with the invention, there are provided pyridine derivatives of the formula:
wherein R represents hydrogen, alkyl or aryl.
Alkyl groups which may be represented by R especially include lower alkyl groups having from one to four carbon atoms and aryl groups especially include phenyl.
The pyridine derivatives of the invention may be prepared by interacting diacetonitrile with malononitrile and an orthoester of the formula: (R'0)3CR2 wherein R1 represents an alkyl radical and R2 represents hydrogen, alkyl or aryl.
Examples of orthoesters which may be used in making the pyridine denvatives nclude triefhyl orthoformate, triethyl orthoacetate and triethyl orthobenzoate.
The method of preparation provides the pyridine derivatives in good yield in a single step synthesis.
The pyridine derivatives are useful chemical intermediates. For example, 4-amino-3,5-dicyano-6- methylpyridine may be reacted with hydrogen sulphide or another agent capable of yielding the hydrosulphide ion to form 3-thiocarbamoyl-4-amino-5-cyano-6-methylpyridine which, in turn, may be oxidised to form 3-amino-6-methyl-7-cyanoisothiazole[4,3-c]pyridine, a useful diazo component for azo dyes.
The invention is illustrated but not limited by the following Example in which all parts are by weight.
Example Diacetonitrile (492 parts) is added to ethanol (1500 parts) and is stirred and warmed to 300C to achieve complete solution.
To this solution at 20"C is added a solution of malononitrile (396 parts) in triethyl orthoformate (888 parts) with stirring. The whole reaction mixture is stirred overnight at room temperature, after which the suspended solid is filtered off, washed with ethanol and dried to give 227 parts of 4-amino3,5-dicyano-6-methylpyridine which is characterised as follows:- M+ 158; I.R. 3360, 3320 (doublet free NH2), 3200-2700 (broad bonded NH2) 2220 (CN), 1660 (C=N) cam~1; N.M.R. (proton) a 2.40 (s./CH3), 7.70 (broad S.2 NH2), 8.35 (s. 1 aromatic H).
Claims
1. A pyridine derivative of the formula:
wherein R represents hydrogen, alkyl or aryl.
2. A method for the preparation of a pyridine derivative as defined in Claim 1 which comprises interacting diacetonitrile with malononitrile and an orthoester of the formula: (R'0)3CR2 wherein R1 represents an alkyl radical and R2 represents hydrogen, alkyl or aryl.
3. A method according to Claim 2 substantially as hereinbefore described with reference to the foregoing Example.
**WARNING** end of DESC field may overlap start of CLMS **.

Claims (3)

**WARNING** start of CLMS field may overlap end of DESC **. SPECIFICATION Pyridine Derivatives This invention relates to pyridine derivatives and more particularly to 4-amino-3,5-dicyano-6methylpyridine and its 2-alkyl and 2-aryi derivatives. Thus, in accordance with the invention, there are provided pyridine derivatives of the formula: wherein R represents hydrogen, alkyl or aryl. Alkyl groups which may be represented by R especially include lower alkyl groups having from one to four carbon atoms and aryl groups especially include phenyl. The pyridine derivatives of the invention may be prepared by interacting diacetonitrile with malononitrile and an orthoester of the formula: (R'0)3CR2 wherein R1 represents an alkyl radical and R2 represents hydrogen, alkyl or aryl. Examples of orthoesters which may be used in making the pyridine denvatives nclude triefhyl orthoformate, triethyl orthoacetate and triethyl orthobenzoate. The method of preparation provides the pyridine derivatives in good yield in a single step synthesis. The pyridine derivatives are useful chemical intermediates. For example, 4-amino-3,5-dicyano-6- methylpyridine may be reacted with hydrogen sulphide or another agent capable of yielding the hydrosulphide ion to form 3-thiocarbamoyl-4-amino-5-cyano-6-methylpyridine which, in turn, may be oxidised to form 3-amino-6-methyl-7-cyanoisothiazole[4,3-c]pyridine, a useful diazo component for azo dyes. The invention is illustrated but not limited by the following Example in which all parts are by weight. Example Diacetonitrile (492 parts) is added to ethanol (1500 parts) and is stirred and warmed to 300C to achieve complete solution. To this solution at 20"C is added a solution of malononitrile (396 parts) in triethyl orthoformate (888 parts) with stirring. The whole reaction mixture is stirred overnight at room temperature, after which the suspended solid is filtered off, washed with ethanol and dried to give 227 parts of 4-amino3,5-dicyano-6-methylpyridine which is characterised as follows:- M+ 158; I.R. 3360, 3320 (doublet free NH2), 3200-2700 (broad bonded NH2) 2220 (CN), 1660 (C=N) cam~1; N.M.R. (proton) a 2.40 (s./CH3), 7.70 (broad S.2 NH2), 8.35 (s. 1 aromatic H). Claims
1. A pyridine derivative of the formula:
wherein R represents hydrogen, alkyl or aryl.
2. A method for the preparation of a pyridine derivative as defined in Claim 1 which comprises interacting diacetonitrile with malononitrile and an orthoester of the formula: (R'0)3CR2 wherein R1 represents an alkyl radical and R2 represents hydrogen, alkyl or aryl.
3. A method according to Claim 2 substantially as hereinbefore described with reference to the foregoing Example.
GB8107274A 1980-04-11 1981-03-09 4-Amino-3,5-dicyano-pyridine Compounds Withdrawn GB2073742A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB8107274A GB2073742A (en) 1980-04-11 1981-03-09 4-Amino-3,5-dicyano-pyridine Compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8012100 1980-04-11
GB8107274A GB2073742A (en) 1980-04-11 1981-03-09 4-Amino-3,5-dicyano-pyridine Compounds

Publications (1)

Publication Number Publication Date
GB2073742A true GB2073742A (en) 1981-10-21

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Family Applications (1)

Application Number Title Priority Date Filing Date
GB8107274A Withdrawn GB2073742A (en) 1980-04-11 1981-03-09 4-Amino-3,5-dicyano-pyridine Compounds

Country Status (1)

Country Link
GB (1) GB2073742A (en)

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