Cook, A. H. published the artcilePreparation of diarylmaleonitriles, Application In Synthesis of 17281-59-3, the publication is Journal of the Chemical Society (1941), 502-6, database is CAplus.
cf. C. and Linstead, C. A. 31, 6237.5. 2,1-HOC10H6CHO (29 g.) and 15 g. of amalgamated Zn in 300 cc. moist ether, boiled overnight and the product treated with HCl, give 310 mg. of 1,2-bis(2-hydroxy-1-naphthyl)ethylene, m. 252°; di-Me ether (I), m. 222°; both give deep red solutions in concentrated H2SO4; light absorption in petr. ether:maximum 3420, 2910 A.; inflection, 2800 A.; E1%1cm. 185, 217, 303, resp. The other products are (2,1-HOC10H6)2CH2 and 24 g. of 2,1-HOC10H6CH2OH (II). II could not be converted to the bromide or iodide. Addition of 25 g. of 2-C10H7OMe in 250 cc. AcOH to a solution of 10 g. (HCHO)3 in 150 cc. AcOH (which had been treated with dry HCl until a clear solution results) and treatment with HCl give, after standing overnight, 21 g. of 2-methoxy-1-chloromethylnaphthalene (III), decomposes at 120° (evolution of HCl); hydrolysis with aqueous NaHCO3 in Me2CO gives 2,1-MeOC10H6CH2OH. Warming III with dilute EtOH-alkali at 40° for several hrs. gives (2-methoxy-1-naphthyl)-carbinyl Et ether, b12 173-5°. III (18 g.) in 600 cc. Me2CO with 12 g. KCN in 300 cc. H2O at 30-5° gives 16 g. of 2-methoxy-1-naphthaleneacetonitrile (IV), m. 111°. III with AgNO3 in Me2CO-EtOH at 30° for 24 h. gives the β-form of I, m. 145°; light absorption in petr. ether: maximum 3380, 2960 A.; inflection 2830 A.; E1%1cm. 180, 270, 300, resp. Both forms give orange colors with concentrated H2SO4; both are unsaturated toward C(NO2)4 but neither is appreciably changed by exposure to UV light in C6H6 solution The 2 ethers are probably cis and trans isomers with relative stabilities not infrequently encountered among isomeric stilbenes. IV in CHCl3 containing CaCO3 gives a Br derivative, m. 145-6°; this did not react with C5H5N. IV does not yield the desired diarylmaleonitrile with Br or I and bases under the most diverse conditions. 2,1-MeC10H6CH2Cl (V) and KCN in 85% EtOH give 2-methyl-1-naphthaleneacetonitrile, m. 78°; when more H2O is used in the reaction, the product is (2-methyl-1-naphthyl)carbinol, m. 137-8°; this loses H2O at 100° in vacuo but could not be reconverted to V with EtOHHCl at room temperature 2,1-MeOC10H6CHO yields a cyanohydrin (VI), m. 111°; with SOCl2 in C6H6 at room temperature for 30 min. VI gives bis[(2-methoxy-1-naphthyl)cyanomethyl] ether (VII), m. 121°. When VI or VII is boiled for 20 min. with an excess of SOCl2, there results 50% of α-chloro-2-methoxy-1-naphthaleneacetonitrile, m. 130°; solution in warm C5H5N gives 1-[(2-methoxy-1-naphthyl)-cyanomethyl]pyridinium chloride (VIII), m. 165° (slight decomposition); aqueous Na2CO3 gives an orange precipitate of 1-[(2-methoxy-1-naphthyl) cyanomethyl] pyridinium enimine-betaine, m. 150° (decomposition); heating at 200°/0.001 mm. liberates C5H5N and gives IV and bis(2-methoxy-1-naphthyl)maleonitrile (IX); passage through Al2O3 gives about 5% of the α form, pale yellow, m. 255°, and 5% of the β form, pale yellow, m. 290°; the yield of IX is much smaller on heating VIII. On heating IX with Cu or Cu salts produces results which give intense green colors in C5H5N with strong absorption of light at 6250 A. ClCH2CN and C5H5N give the very deliquescent (cyanomethyl)pyridinium chloride (X), m. 178°; aqueous KOH or K2CO3 gave the yellow betaine, which easily resinified and could not be crystallized X and Bz2O in CHCl3, shaken with aqueous K2CO3, give the light yellow Bz derivative of the betaine, m. 145°, identical with Kröhnke’s (ω-cyanophenacyl)pyridinium benzoate (C. A. 33, 2522.9). ClCH2CONH2 gives acetamidopyridinium chloride, m. 202-3°; it gives no betaine with alkali. PhClCHCN in C5H5N gives (α-cyanobenzyl)pyridinium chloride (XI), m. 159°. The red enimine-betaine, sublimed at 120° in vacuo, gives about 50% of diphenylmaleonitrile; distillation of XI in vacuo gives about 10%. It appears, therefore, that dimerization proceeds only with arylhaloacetonitriles. PhCH2CH(OH)CN and PCl5 in C6H6, warmed until solution results, give 62% of α-chloro-β-phenylpropionitrile, b13 128-30°; boiling with quinoline gives PhCH:CHCN in practically quant. yield. PhCH:CH(OH)CN and SOCl2 give a product b15 130-40°; this is mainly α-chloro-γ-phenylvinylacetonitrile, but it could not be obtained pure because it continually deposits a compound m. 114°, probably 2,5-diphenyldihydroterephthalonitrile; it yielded no porphyrazine pigment. p-MeOC6H4CH(OH)CN (12 g.) and 10% excess of SOCl2 give 7 g. of (p-methoxyphenyl)-chloroacetonitrile (XII), b13 153-5°; sublimation of the residue in the distillation flask in vacuo gives bis(p-methoxyphenyl)maleonitrile, m. 186-7°; this also is formed by the direct action of C5H5N on XII. A C5H5N solution of the melt obtained on heating with Fe at 300° is an intense green color and showed characteristic porphyrazine spectral absorption bands (6320, 5800 A.).
Journal of the Chemical Society published new progress about 17281-59-3. 17281-59-3 belongs to pyridine-derivatives, auxiliary class Pyridine,Nitrile,Salt, name is 1-(Cyanomethyl)pyridin-1-ium chloride, and the molecular formula is C7H7ClN2, Application In Synthesis of 17281-59-3.
Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem