Anderson, D. M. W.; Bell, F.; Duncan, J. L. published an article in 1961, the title of the article was Some condensation products of malononitrile.Reference of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile And the article contains the following content:
Malononitrile (I) was condensed with a variety of carbonyl compounds, and the infrared spectra of the products recorded. I and Me2CO gave isopropylidenemalononitrile (II), b10 98°. The residue from the distillation formed a yellow powder, decomposed at 300°. Interaction of Me2CO with I gave a yellow K salt, and decomposition with AcOH gave plates, decomposed at 170° with evolution of isobutcne. This yielded a yellow powder as above. II was soluble in aqueous NH4OH. NHEt2 (0.2 cc.) in 2 cc. Me2CO added to 25 cc. Me2CO and 5 g. I, left overnight, and the product crystallized gave 2.4 g. of the isopropylidenemalonouitrile dimer (III), prisms, m. 171-4°. The solution contained Me2CO, identified as the 2,4-dinitrophenylhydrazone. If in this reaction the concentration of I was raised, the principal product was no longer III but the compound which decomposed at 170°. NHEt2 (0.2 cc.) in 2 cc. alc. kept 2 hrs. at 70° with 3 cc. mesityl oxide and 1.7 g. I in 5 cc. alc. gave 1.1 g. of the product, m. 170° (decomposition). II was treated with piperidine or in C6H6 solution of piperidine or in Me2CO solution with NHEt2; in each case the product disintegrated at 170°. Mesityl oxide did not react with I under the conditions used to prepare II. No condensation product was isolated from a mixture of phorone and I containing NHEt2. No reaction occurred between III and Me2CO with NHEt2. Condensation in alc. by KOEt also failed. When NH4OH was added to a solution of 3 g. I in 5 cc. Me2CO the mixture became hot and set to a yellow crystalline mass. acidification and isolation gave malononitrile trimer. Schenck’s I trimer, prepared by the action of dry NH3 on C6H6 suspension of I, crystallized to give a product, m. 220-4°. When I trimer was heated to 230° violent change occurred; the residual mass was extracted with refluxing C5H5N and diluted with alc.; and the product, unmelted at 360° was obtained as yellow crystals from refluxing HCO2H. I (1 g.) added to 1 cc. NHEt2 became very hot and treatment with dilute HCl gave a dimer, m. 168-70°. Submission of I to Schenck’s method for a trimer gave only a dimer, m. 170°. This dimer heated to 200° underwent complex decomposition Acetophenone (4 cc.) and 2 g. I containing a few drops NHEt2 kept warm a few hrs., cooled, and the product crystallized gave 1,1-dicyano-2-methyl2-phenylethylene (IV), m. 94°, and canary yellow needles of an isomer (V), m. 205-7°. IV could be partially converted into V by heating 3 hrs. at 70° in the presence of some NHEt2. The spectrum of V did not agree with the expected 4-amino-1,1,5-tricyano-2,6-diphenylhepta-1,3,5triene. Et α-cyano-1-indanylideneacetate formed needles, m. 100-2°; Me ester m. 142-4°. Refluxing I and indanone in C5H5N or alc. containing a drop piperidine gave 1-dicyanomethyleneindan (VI), m. 152°. 2-(1′-Indanylidene)indan1-one was unchanged after reflexing with I, I dimer, or Et cyanoaeetate in alc. K2CO3 (3 g.) added to 2 g. 1-indanone and 1.5 g. I in alc. and warmed 10 min. gave a compound as yellow prisms, m. about 250°. K2CO3 (2.5 g.) refluxed 0.5 hr. with 1.3 g. indanone and 1.8 g. IV in 40 cc. alc., a small amount VI filtered off, and the filtrate acidified and recrystallized gave a compound, m. 250-5°. Fluorenylidenemakmo nitrile from AcOH formed red needles, m. 234-5°. Benzophenone and I gave 1,1-dicyano-2,2-diphenylethylene, m. 138°. NHEt2 added to a mixture of 2.1 g. benzoin and 1.4 g. I in 20 cc. alc., left 2 hrs. and cooled gave 0.7 g. benzil and the filtrate afforded needles, m. 204-6°. NHEt2 (0.2 g.) added to 2.1 g. benzil and 1.4 g. I in 25 cc. alc. and kept 2 hrs. at 70° gave 2-amino-4-benznyl-1,1,3-tricyano-4phenylbutadiene, m. 195° (decomposition). Condensation of benzil and Et cyanoaectate gave Et α-cyano-β-benzoyl-Cinnamate, prisms, m. 139-41°, and a compound suspected of being Et α,γ-dicyano-β-phenylbenzoylglutarate, prisms, m. 169-71°. NHEt2, 2.1 g. benzil, and 1.7 g. cyanoacetamide kept in alc. overnight gave a product, prismatic needles, m. 167-70°. 3-Dicyanomethyleneoxindole when refluxed 1 hr. with Ac2O gave the N-acetyl derivative, m. 170°. Addition of anhydrous K2CO3 to a refluxing suspension of 1 g. isatin in 10 cc. MeOH containing 1 cc. Me cyanoacetate gave Me α-cyano3-oxindolylideneacetate, m. 240-2° (decomposition); N-acetyl derivative, yellow crystals, m. 147-9°. Addition of I to a refluxing alc. solution of 5-methylisatin gave 5-methyl-3-dicyanomethyleneoxindole, m. 260°; N-acetyl derivative m. 198-200°. Treating 1 g. 5-methylisatin and 1 g. I dimer in 20 cc. alc. gave red crystals of 3-(2-amino-1,3,3-tricyanoallylidene)-5methyloxindole, m. 333° (decomposition). Anhydrous K2CO3 (3 g.) added to a refluxing mixture of 2 g. acenaphthenequinone (2 g.) and 2 g. I in 100 cc. alc., left 0.5 hr., and diluted with 100 cc. hot H2O, followed by extraction by Soxhlet gave a blueblack product, decomposed above 300°. NHEt2 added to 1 g. phenanthraquinone and 1 g. I in 200 cc. alc. gave a black product, decomposed at 300°. N-(α-Cyanobenzylidene)-phydroxyaniline was prepared Too long contact with alc.NaOH gave conversion into p-hydroxybenzanilide, m. 214°. By the same method 3-methyl-4-nitrosophenol gave N-(α-cyanobenzylidene)-4-hydroxy-2-methylaniline, yellow needles, m. 198-200°, and 2-methyl-4-nitrosophenol gave N-(α-cyanobenzylidene)-4-hydroxy-3-methylaniline, m. 142-4° (alc.) The experimental process involved the reaction of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile(cas: 2510-01-2).Reference of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile
2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile(cas:2510-01-2) belongs to nitriles. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Reference of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts