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Chemical Structure| 64379-45-9

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Product Details of [ 64379-45-9 ]

CAS No. :64379-45-9
Formula : C9H6N2O
M.W : 158.16
SMILES Code : O=CC1=CC=C2C=CC=NC2=N1
MDL No. :MFCD04971934
InChI Key :TXEQVJDZTRPUKO-UHFFFAOYSA-N
Pubchem ID :2050090

Safety of [ 64379-45-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501

Application In Synthesis of [ 64379-45-9 ]

* 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 [ 64379-45-9 ]

[ 64379-45-9 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1569-16-0 ]
  • [ 64379-45-9 ]
YieldReaction ConditionsOperation in experiment
60% With selenium(IV) oxide; water; In 1,4-dioxane;Reflux; A flask was charged with SeO2 (1.3 g, 11.7 mmol), 1,4-dioxane (20 mL) and a few drops of water. After the solution was refluxed for a few minutes, <strong>[1569-16-0]2-methyl-1,8-naphthyridine</strong> (1 g, 6.9 mmol) was slowly added and the mixture turned red. The solution was then maintained at then continuing refluxed for another 3 h and during this time the red solution changed to brownish black. The hot solution was then filtered and the solvent was removed in vacuum. The resulting residue was dissolved in CH2Cl2, washed with water (3 x 30 mL), dried over Na2SO4 and concentrated under vacuum to give a brown solid. m.p. 65-68 °C. Yield: 60percent (0.67 g, 4.2 mmol). 1H-NMR (400 MHz, CDCl3) delta (ppm): 10.32 (s, 1H), 9.28-9.27 (m, 1H), 8.40 (d, J = 8.4 Hz, 1H), 8.32 (dd, J = 8.4 Hz, J = 1.2 Hz, 1H), 8.15 (d, J = 8.4 Hz, 1H), 7.63 (dd, J = 8.4 Hz, J = 4 Hz, 1H). 13C-NMR (100 MHz, CDCl3) delta: 193.5, 155.6, 155.4, 154.9, 138.8, 137.1, 125.2, 124.0, 118.3 ppm. Anal. Calcd for C9H6N2O: C 68.35; H 3.82, N 17.71. Found: C 68.21; H 3.56, N 17.85.
56.6% With selenium(IV) oxide; In 1,4-dioxane; for 4h;Reflux; Inert atmosphere; 2-Methyl-1,8-naphthyridine (1.1592 g, 8.0 mmol) and SeO2 (1.2452 g, 11.2 mmol) were added to 20 mL of 1,4-dioxane. The mixture were refluxed for 4 h in nitrogen atmosphere and filtered. The filtrate was concentrated in vacuum to give the crude product and the final product was obtained by column chromatography (200-300 mesh, ethyl acetate) (0.71 g, 56.6percent yield). Characterization of 1,8-naphthyridine-2-aldehyde: HRMS (EI) m/z: calcd for C9H7N2O [M+H]+, 159.0588; found, 159.0561. 1H NMR: (400 MHz; DMSO; TMS) 10.15 (s, 1H), 9.24-9.26 (m, 1H), 8.71 (d, 1H), 8.60-8.62 (m, 1H), 8.08 (d, 1H), 7.78-7.80 (m, 1H). 13C NMR (100 MHz, DMSO): 194.3, 155.8, 155.5, 155.0, 140.5, 138.3, 125.6, 124.9, 118.5.
With selenium(IV) oxide; In 1,4-dioxane; at 80 - 130℃;Inert atmosphere; <strong>[1569-16-0]2-methyl-1,8-naphthyridine</strong> (288 mg, 2 mmol) and twice the equimolar amount of selenium dioxide (221.92 mg-443.84 mg, 2 mmol-4 mmol) was dissolved in 50 ml of 1,4-dioxane under nitrogen or without nitrogen protection at 80 ° C to 130 ° C for 8-16 hours. During the reaction, the silica gel plate was detected at any time until the basic reaction of <strong>[1569-16-0]2-methyl-1,8-naphthyridine</strong> was completed and a new point was generated. After completion of the reaction, the reaction mixture was suspended, purified on silica gel column with dichloromethane to obtain 1,8-naphthyridine-2-aldehyde.
With selenium(IV) oxide; In 1,4-dioxane; water; at 0 - 100℃; for 5h; A solution of selenium dioxide (8.61 g, 77.56 mmol) in 1,4 dioxane (140 mL) with 0.5 mL ofwater was stirred at 100 °C for 5 mm. The mixture was cooled down to 0 °C and 2-Methyl-I ,8-naphthyridine (7 g, 48.5 mmol) was added dropwise. The mixture was heated again at100 °C for 5 h. Completion of the reaction was monitored by TLC. The reaction mixturewas filtered through celite bed, washed with EtOAc (50 mL) and concentrated. Theresulting crude mixture was dissolved in EtOAc (150 mL) and washed with water (3 x 60mL), brine (30 mL), dried over Na2SO4 and concentrated to give the title compound (brownsolid). 1H NMR (300 MHz, DMSO-d6): 6 10.18 (5, IH), 9.28-9.27 (m, IH), 8.74 (d, J = 8.1 Hz, IH), 8.63 (d, J= 8.1 Hz, IH), 8.11 (dd, J= 8.4, 1.2 Hz, IH), 7.83-7.79 (m, IH). LCMS:(Method B) 159.0 (M +H), Rt. 2.44 mm, 91 .59percent (Max). HPLC: (Method B) Rt 2.41 mm, 87.86percent (Max).
With selenium(IV) oxide; In 1,4-dioxane; water; at 0 - 100℃; for 5h; A solution of selenium dioxide (8.61 g, 77.56 mmol) in 1 ,4 dioxane (140 mL) with 0.5 mL of water was stirred at 100 °C for 5 min. The mixture was cooled down to 0 °C and 2-Methyl- 1 ,8-naphthyridine (7 g, 48.5 mmol) was added dropwise. The mixture was heated again at 100 °C for 5 h. Completion of the reaction was monitored by TLC. The reaction mixture was filtered through celite bed, washed with EtOAc (50 mL) and concentrated. The resulting crude mixture was dissolved in EtOAc (150 mL) and washed with water (3 x 60 mL), brine (30 mL), dried over Na2SO4 and concentrated to give the title compound (brown solid). 1H NMR (300 MHz, DMSO-d6): delta 10.18 (s, 1 H), 9.28-9.27 (m, 1 H), 8.74 (d, J = 8.1 Hz, 1 H), 8.63 (d, J = 8.1 Hz, 1 H), 8.1 1 (dd, J = 8.4, 1.2 Hz, 1 H), 7.83-7.79 (m, 1 H). LCMS: (Method B) 159.0 (M +H), Rt. 2.44 min, 91.59percent (Max). HPLC: (Method B) Rt 2.41 min, 87.86percent (Max).

 

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