15119-34-3|2-Oxo-2H-chromene-3-carbonitrile| Ambeed

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Quality Control of [ 15119-34-3 ] Purity: 98% SDS Specification

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Product Details of [ 15119-34-3 ]

CAS No. :	15119-34-3
Formula :	C₁₀H₅NO₂
M.W :	171.15
SMILES Code :	O=C1OC2=C(C=CC=C2)C=C1C#N
MDL No. :	MFCD00115699
InChI Key :	QKJALQPLNMEDAV-UHFFFAOYSA-N
Pubchem ID :	203763

Safety of [ 15119-34-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Application In Synthesis of [ 15119-34-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 15119-34-3 ]

[ 15119-34-3 ] Synthesis Path-Downstream 1~36

1
[ 36937-71-0 ]
[ 15119-34-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; water; at 75℃; for 1h;	0.1 mol of salicylaldehyde was mixed into 10 ml of water, and a small amount of ammonium acetate was added to the mixture under stirring. 0.15 mol of malononitrile was added to the mixture at room temperature and reacted at room temperature for 2 hours. After the reaction is complete, add enough dilute hydrochloric acid to acidify and filter, and dry. The product is then suspended in 10 ml of 2N dilute hydrochloric acid and the suspension is heated to 75 degrees with stirring. The reaction is carried out for 1 hour. After completion of the reaction, the mixture is filtered, dried, and the product is washed twice with a small amount of methanol to obtain a pale yellow solid. Product, yield 58%.

References: [1]Journal of Heterocyclic Chemistry,2009,vol. 46,p. 1392 - 1395.
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2005,vol. 44,p. 1307 - 1308.
[3]Journal of the Chemical Society,1953,p. 119,121.
[4]Journal of Organic Chemistry,1984,vol. 49,p. 5195 - 5197.
[5]Synthesis,2003,p. 2331 - 2334.
[6]Archiv der Pharmazie,2011,vol. 344,p. 588 - 594.
[7]Journal of Molecular Liquids,2014,vol. 195,p. 240 - 247.
[8]Patent: CN108069929,2018,A .Location in patent: Paragraph 0048; 0098-0100.

2
[ 90-02-8 ]
[ 105-56-6 ]
[ 15119-34-3 ]

Yield	Reaction Conditions	Operation in experiment
98%	With zirconyl chloride octahydrate; sodium amide; In tetrahydrofuran; at 25℃; for 0.5h;Green chemistry;	General procedure: A mixture of salicylaldehyde (1, 1 mmol), active methylene compound (2, 1.2 mmol), ZrOCl2-THF (0.048 g, 0.15 mmol) and sodium amide (0.005 g, 0.15 mmol) was stirred for 30 min at room temperature. The progress of the reaction was monitored by TLC. After the completion of reaction, the crude mixture was diluted with moist ether (20 mL). The resultant reaction mixture was washed with water (3 × 25 mL) to discharge the colour, ZrOCl2 and sodium amide. The ethereal solution obtained after extraction was dried over anhydrous Na2SO4 and evaporated under reduced pressure. Finally, this reaction mixture was purified by passing through a silica gel column chromatography to get pure product (Scheme-I).
92%	With [bis(acetoxy)iodo]benzene; In ethanol; at 35 - 40℃; for 0.5h;	General procedure: α-substituted ethyl acetate (1.0 mmol)and Phenyliododiacetate (1.0 mmol) was dissolved in ethanol (5 ml) with constant stirring. After 10 minutes benzaldehyde/salicylaldehyde (1.0 mmol), was added and the mixture was allowed to stir for appropriate time. Then the progress of the reaction was monitored by thin layer chromatography. After completion of reaction as indicated by TLC, ethanol was evaporated under reduce pressure. The product was extracted with ethyl acetate, dried over Na2SO4 and solvent was evaporated under reduce pressure. The residue obtained was recrystallized by ethyl acetate and hexane to product 3a-3h and 4a-4r.
91%	With L-proline; at 20℃; for 0.25h;Green chemistry;	General procedure: A mixture of a salicylaldehyde 1 (10 mmol), activemethylene compound 2 (12 mmol) and 25 mol% of Lprolinein triethanolamine (5 mL) was stirred at room temperaturefor the appropriate time as indicated in (Table 4).The progress of the reaction was monitored by TLC. Afterthe completion of reaction, the mixture was poured into icecoldwater (50 mL). The separated solid was filtered, washedwith water and dried. The crude product was recrystallizedfrom a suitable solvent to obtain pure 3. 1H NMR and 13CNMR data of the prepared compounds is given below:

91%	With Zeolitic imidazolate framework (ZIF-8); In N,N-dimethyl-formamide; at 80℃; for 8h;	General procedure: 34. A typical experimental procedure for the ZIF-8 catalyzed synthesis of3-cyanocoumarins. In a Pyrex screw-cap tube, the 2-hydroxy aromaticaldehyde (0.5 mmol) was dissolved in 5 mL of DMF. The ZIF-8 catalyst(18 mg, 16 mol%) was added and the mixture stirred for 5 min. Ethylcyanoacetate (3 mmol) was then injected. The reaction mixture was heatedat 80 C for the time indicated in Table 2 and the progress of the reaction wasmonitored by TLC. After complete conversion, as indicated by TLC, the reactionmixture was cooled to room temperature and the ZIF-8 was separated bycentrifugation. The organic was concentrated under reduced pressure and thecrude reaction mixture was directly charged onto a small silica gel column andeluted with a mixture of ethyl acetate/petroleum ether to afford the pure3-cyanocoumarin 2.
90%	With potassium phtalimide; In water; at 20℃; for 2.5h;Green chemistry;	General procedure: Salicylaldehyde derivative (1 mmol), active methylene compound (1 mmol) and PPI were added to 5 mL of water and the reaction mixture was stirred at room temperature for the appropriate time (Table 2). After completion of the reaction (as indicated by TLC analysis), the mixture was filtered to separate the precipitated product, which was further purified by rinsing with cold reaction solvent. The filtrate was charged with the same substrates and was reused for successive cycles. The products were identified by comparison with authentic samples or NMR data. 2-Oxo-2H-chromene-3-carbonitrile (4a). IR (KBr) (max, cm-1): 3042, 2224, 1770, 1725, 1682, 1605, 1560; 1H NMR (300 MHz, CDCl3) δ: 8.35 (s, 1H, CH), 8.35 (s, 1H), 7.64 (t, J = 7.5 Hz, 1H, ArH), 7.59 (d, J = 7.6 Hz, 1H, ArH), 7.36-7.44 (m, 2H, ArH); 13C NMR (75MHz, CDCl3) δ: 159.4, 156.5, 135.6, 130.4, 128.3, 125.2, 120.3, 118.5, 114.5, 101.8 ppm.
88%	With barium(II) hydroxide; In ethanol; water; for 1h;Sonication; Green chemistry;	General procedure: A mixture of substituted2-hydroxybenzaldehydes or 2-hydroxyacetophenone(2 mmol), ethyl cyanoacetate (2 mmol), and activatedbarium hydroxide (2 mmol) in 20 mL of aqueousethanol (1:1) was subjected to dual-frequency ultrasonicirradiation by placing the beaker containing thereaction mixture into an ultrasonic bath and simultaneously putting a probe type ultrasonicator into thesame beaker for 60 min. Thin-layer chromatographywas used to monitor the reaction progress. The solidproduct was filtered off, washed with water, and recrystallizedfrom methanol.2-Oxo-2H-chromene-3-carbonitrile (1a). Yield88%, mp 180-181C; published data [29]: mp 179-181C. IR spectrum (KBr), cm-1: 2228 (C≡N), 1725(C=O). 1H NMR spectrum (CDCl3), δ, ppm: 7.38 m(2H, 6-H, 7-H), 7.68 d.d (1H, J = 7.42, 1.44 Hz),7.75 d.d (1H, J = 7.48, 1.54 Hz), 8.75 s (1H, 4-H).
5%Spectr.	With 2a immobilized on mesoporous silica SBA-15; In ethanol; at 60℃; for 6h;	General procedure: In a 10 mL round bottom flask, 3.0 mmol of salicaldehyde was introduced, followed by 5 mol% of base catalyst and β-methoxynaphtalene (as internal standard). Then 30.0 mmol of activated methylene was added, followed by 4.5 mL of anhydrous EtOH. The mixture was heated to 60 C for six hours and then the reaction was quenched by the addition of 10 μL of 4 MHCl solution in 1,4-dioxane. Volatiles were reduced in vacuum and the residue was dissolved in CDCl3 to allow the estimation of the yield by NMR quantification.

References: [1]Asian Journal of Chemistry,2020,vol. 32,p. 2611 - 2616.
[2]Chemistry - A European Journal,2012,vol. 18,p. 8659 - 8672.
[3]Journal of the Iranian Chemical Society,2016,vol. 13,p. 149 - 153.
[4]Tetrahedron Letters,2017,vol. 58,p. 3183 - 3187.
[5]Letters in Organic Chemistry,2014,vol. 11,p. 556 - 563.
[6]Tetrahedron Letters,2016,vol. 57,p. 5885 - 5888.
[7]Bulletin of the Chemical Society of Ethiopia,2015,vol. 29,p. 449 - 456.
[8]Russian Journal of Organic Chemistry,2021,vol. 57,p. 1508 - 1512.
Zh. Org. Khim.,2021,vol. 57,p. 91508 - 91512.
[9]Journal of Heterocyclic Chemistry,2007,vol. 44,p. 867 - 870.
[10]Journal of Chemical Research - Part S,1998,p. 468 - 469.
[11]Asian Journal of Chemistry,2011,vol. 23,p. 235 - 238.
[12]Angewandte Chemie - International Edition in English,1997,vol. 36,p. 2661 - 2663.
[13]Proceedings - Indian Academy of Sciences, Section A,1942,p. 29,34.
[14]Chemical Communications,2010,vol. 46,p. 746 - 748.
[15]Catalysis Communications,2012,vol. 28,p. 1 - 4.
[16]Organic and Biomolecular Chemistry,2015,vol. 13,p. 1307 - 1312.
[17]ACS Catalysis,2017,vol. 7,p. 613 - 630.
[18]Pharmaceuticals,2021,vol. 14.

3
[ 52218-17-4 ]
[ 15119-34-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; trichlorophosphate; In 1,4-dioxane; at 10℃; for 10.25h;Reflux;	A solution of phosphoryl chloride (0.5 mL, 5 mmol) in dry 1,4-dioxane (5 mL) was added dropwise to compound 1 (0.94 g, 5 mmol) in dry 1,4-dioxane (25 mL) in the presence of catalytic amount of triethylamine (1.91 mL, 10 mmol) or in pyridine (25 mL) for 15 min at 10 C. The mixture was heated under reflux for 10 h. The reaction mixture was cooled and poured into cold water. The formed solid was filtered off, washed with water and crystallized from diluted EtOH to give white solid in 38-45% yield; mp 140-142 C (Lit.19 144-146 C). IR (KBr), (v max, cm-1): 3051 (C-Harom), 2240 (C≡N), 1734 (C=O), 1607, 1562 (C=C), 1049 (C-O). 1H-NMR (400 MHz, DMSO-d6): 7.45 (t, 1H, J=7.6 Hz, H-6), 7.49 (d, 1H, J=8.4 Hz, H-8), 7.76-7.80 (m, 2H, H-7 and H-5), 8.93 (s, 1H, H-4).

References: [1]Journal fur praktische Chemie (Leipzig 1954),1981,vol. 323,p. 691 - 693.
[2]Heterocycles,2019,vol. 98,p. 681 - 692.

4
[ 15119-34-3 ]
[ 57331-59-6 ]
[ 95633-55-9 ]

References: [1]Bulletin de la Societe Chimique de France,1984,vol. 2,p. 338 - 344.

5
[ 6968-92-9 ]
[ 15119-34-3 ]

References: [1]Tetrahedron,1991,vol. 47,p. 9297 - 9304.

6
[ 90-02-8 ]
[ 109-77-3 ]
[ 15119-34-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With iodine; In N,N-dimethyl-formamide; for 0.0333333h;Microwave irradiation;	General procedure: Method B (microwave conditions): A mixture of 2-hydroxybenzaldehydes/2-hydroxyacetophenones1a-i (4.71 mmol), malononitrile (2, 0.32 g, 4.71 mmol), iodine (0.03 g, 0.12mmol) and dimethylformamide (5 mL) taken in a loosely stoppered round bottom flask wassubjected to microwave irradiation for 2-5 min. Completion of the reaction was controlled bythin layer chromatography (silica gel plates using the solvent benzene: acetone, 1:1). The reaction mixture wascooled and ice-cold sodium thiosulphate solution (10 %, 30 mL) was added to remove anyiodine present in the reaction mixture. The solid that separated out was filtered, washed withwater and recrystallised from aqueous ethanol to give 3a-i.
72%	With ferric(III) chloride; In ethanol; at 80℃; for 24h;Mechanism;	General procedure: To a stirred solution of salicyladehyde 1 (1 mmol) and the activated methylene compounds 2 (1.2 mmol) in ethanol (3 mL) was added anhydrous FeCl3 (0.05mmol). The mixture was heated in an oil bath at 80 C for 24 h and cooled down to room temperature. The solvent was removed under vacuum, and the residue was directly purified by flash column chromatography on silica gel (200-300 mesh) with ethyl acetate and petroleum ester (1:6-1:8, v/v) as eluting solvent to afford the product 3.

References: [1]ARKIVOC,2012,vol. 2012,p. 242 - 253.
[2]Heterocycles,2010,vol. 80,p. 631 - 636.
[3]Journal of the Serbian Chemical Society,2014,vol. 79,p. 527 - 531.
[4]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1998,vol. 37,p. 936 - 938.
[5]Journal of Organic Chemistry,2008,vol. 73,p. 1954 - 1962.
[6]Journal of Heterocyclic Chemistry,2011,vol. 48,p. 799 - 802.
[7]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 498 - 507.
[8]Synthetic Communications,2014,vol. 44,p. 1507 - 1514.
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[10]Heterocycles,1996,vol. 43,p. 1257 - 1266.
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[13]Journal of Organic Chemistry,2020,vol. 85,p. 1193 - 1201.
[14]New Journal of Chemistry,2022,vol. 46,p. 5034 - 5042.

7
[ 15119-34-3 ]
2-thioxo-3-cyano-2H-chromene [ No CAS ]

References: [1]Chemistry of Heterocyclic Compounds,1996,vol. 32,p. 773 - 776.

8
[ 3949-36-8 ]
[ 140-87-4 ]
[ 15119-34-3 ]