2-Aminopyridine derivatives prepared by reacting a quaternary ammonium compound with malononitrile in the appearance of an alkanol, replaced by reaction with ammonia in the behavior of an alkanol, water and ether to give aminonicotinonitrile and, if wanted, then reacting this product with an alkali metal compound to provide aminonicotinic acid.
The 2-aminopyridine derivatives available by the process of the invention are valuable starting materials for the preparation of pesticides, drugs, vitamins, and dyes.
CAS number 504-29-0
EC number 207-988-4
Hill Formula C₅H₆N₂
Chemical formula 2-(NH₂)C₅H₄N
Molar Mass 94.11 g/mol
HS Code 2933 39 99
The prepared invention relates to a process for the preparation of 2-aminopyridine derivatives by reacting a quaternary ammonium compound with malononitrile in the appearance of an alkanol, followed by reaction with ammonia in the attendance of an alkanol, water and/or an ether to give aminonicotinonitrile and, if wanted, then reacting this product with an alkali metal compound to provide aminonicotinic acid.
The formation of quaternary ammonium compounds, which are also derivatives of malonaldehyde, of the formula ##STR1## where R4 is alkyl and R5 is alkyl or H, by using phosgene with a dialkyl formamide to give a dialkylformamidechloride and then reacting the product with an enol ether has been disclosed (German Laid-Open Application DOS 2,424,373).
Moreover, it is known (Synthesis 1979, pages 376 to 378) that alkylidene malodinitriles can be found with lithium-diisopropylamide in tetrahydrofuran at -65° C. and the product then replied with dimethylformamide dichloride to give 4-dimethylamino-1,3-butadiene-1,1-carbonitrile. These butadiene mixtures can be changed to 2-aminopyridines by reaction with ammonia in methanol.
Similarly, as reported in German Laid-Open Application DOS 1,811,973, 2-amino-5,6-dihydro-4-methylthiobenzoquinoline-3-carbonitrile is obtained by reacting 2-methylthio-2-(3,4-dihydro-1-pyrrolidine-2-naphthyl)-ethylene-1,1-dicarbonitrile with aqueous ammonia in the presence of methanol.
It observed that 2-aminopyridine derivatives of the formula ##STR2## where R1 is cyano or carboxyl, are advantageously obtained if a quaternary ammonium compound of the formula ##STR3## where the different radicals R2 and R3 can be identical or different and each is an aliphatic radical,
(a) is found with malononitrile in the presence of an alkanol,
(b) the resulting reaction mixture is then exposed with ammonia in the presence of an alkanol, water, and ether and if desired,
(c) the aminonicotinonitrile thus obtained is taken with an alkali metal compound.
Related Categories Alphabetical, Biochemicals and Building Blocks, Reagents, C5,
InChI Key ICSNLGPSRYBMBD-UHFFFAOYSA-N
bp 204-210 °C(lit.)
mp 54-58 °C (lit.)
Signal word Danger
Hazard statements H301 + H311-H315-H319-H335
Precautionary statements P261-P280-P301 + P310-P305 + P351 +
Personal Protective Equipment Face Shields, Eyeshields, Gloves, type P2 (EN 143)
RIDADR UN 2671 6.1 / PGII
WGK Germany 3
Flash Point(F) 197.6 °F
Flash Point(C) 92 °C
R Phrase R 23/24/25-51/53
Toxic by inhalation, in touch with skin and if eaten. Toxic to aquatic organisms, may cause long-term adverse results in the marine environment.
In case of touch with eyes, rinse quickly with plenty of water and seek medical advice. Wear proper protective clothing and gloves. In case of disaster or if you feel unwell, ask medical advice quickly (show the label where possible). Avoid release to the situation. Refer to individual instructions/ Safety data sheets. There are many API manufacturers in global that provide all the states to utilize.
Application: 2-Aminopyridine for structure. CAS 504-29-0, analytic formula 2-(NH₂)C₅H₄N.