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Chemical Structure| 30489-44-2 Chemical Structure| 30489-44-2

Structure of 30489-44-2

Chemical Structure| 30489-44-2

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Product Details of [ 30489-44-2 ]

CAS No. :30489-44-2
Formula : C9H10N2O
M.W : 162.19
SMILES Code : OCC1=C(C)N=C2C=CC=CN21
MDL No. :MFCD07368506

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Application In Synthesis of [ 30489-44-2 ]

* 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 [ 30489-44-2 ]

[ 30489-44-2 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 2549-19-1 ]
  • [ 30489-44-2 ]
YieldReaction ConditionsOperation in experiment
Under nitrogen atmosphere, to a suspension of aluminum lithium hydride (1.6 g) in THF (100 ml) was added dropwise a solution of <strong>[2549-19-1]ethyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate</strong> (8.56 g) in THF (100 ml) at 0C under nitrogen atmosphere. The mixture was stirred for 1 hour at 0C, water (1.6 ml), 15% aqueous solution of sodium hydroxide (1.6 ml) and water (4.8 ml) were sequentially and slowly added dropwise to the solution, and the mixture was stirred for 2 hours at room temperature. To the reaction solution was added magnesium sulfate, and the precipitates were removed by filtration. The mixture was concentrated under reduced pressure, to give 2-methylimidazo[1,2-a]pyridine-3-methanol (6.45 g) as pale yellow amorphous. A mixture of 2-methylimidazo[1,2-a]pyridine-3-methanol (1 g) and 4-aminothiophenol (0.65 g) in concentrated hydrochloric acid (10 ml) was stirred for 18 hours at room temperature. 8N aqueous solution of sodium hydroxide was added to adjust pH to 10 at 0C and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was separated and purified by column chromatography (ethanol:ethyl acetate 1:4), to give 3-(4-aminophenylthiomethyl)-2-methylimidazo[1,2-a]pyridine (311 mg) as colorless crystals. m.p. 162 to 164C 1H-NMR (200 MHz, CDCl3) δ 2.00 (3H, s), 3.62 to 3.81 (2H, m), 4.15 (2H, s), 6.49 (2H, d, J = 8.5 Hz), 6.79 to 6.87 (1H, m), 6.92 (2H, d, J = 8.5 Hz), 7.13 to 7.22 (1H, m), 7.49 to 7.55 (1H, m), 8.00 to 8.04 (1H, m) IR (KBr) 3335, 3175, 1597, 1495, 1350, 1296, 1254, 829 cm-1 Elemental Analysis for C15H15N3S·0.2H2O Calcd. C, 66.00; H, 5.69; N, 15.39: Found. C, 66.17; H, 5.69; N, 15.11.
 

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