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Chemical Structure| 39267-53-3 Chemical Structure| 39267-53-3

Structure of 39267-53-3

Chemical Structure| 39267-53-3

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Product Details of [ 39267-53-3 ]

CAS No. :39267-53-3
Formula : C10H11NO4
M.W : 209.20
SMILES Code : O=C(OC)C1=CC=C(NC(C)=O)C(O)=C1
MDL No. :MFCD17015529

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Application In Synthesis of [ 39267-53-3 ]

* 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 [ 39267-53-3 ]

[ 39267-53-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 39267-53-3 ]
  • [ 136663-23-5 ]
YieldReaction ConditionsOperation in experiment
In acetic acid; for 6.0h;Heating / reflux; 11.0 g of methyl 4-amino-3-hydroxybenzoate (CAS No. 63435-16-5, purchased from Lancaster) was dissolved in xylene (220 ml)-tetrahydrofuran (110ml) at room temperature. To this solution, acetyl chloride (4.73 ml) was added and heated to reflux for 6 hours. The mixture was partitioned between 1N aqueous hydrochloric acid and ethyl acetate and the ethyl acetate layer was separated. The ethyl acetate layer was washed with saturated aqueous sodium chloride, and then dried with magnesium sulfate. The mixture was filtrated, and the filtrate was concentrated under reduced pressure. The obtained residue was passed through a silica gel flash chromato (ethyl acetate/heptane system) to obtain 10 g of methyl 4-acetamide-3-hydroxybenzoate crude product. To the crude product, acetic acid (250 ml) was added and heated to reflux for 6 hours, and the mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate, and the ethyl acetate layer was separated. The ethyl acetate layer was dried with magnesium sulfate, filtrated through NH silica gel, and the filtrate was concentrated under reduced pressure to obtain 9.52 g of 2-methyl-6-benzoxazole carboxylic acid methyl ester. To the obtained 2-methyl-6-benzoxazole carboxylic acid methyl ester (9.52 g), ethanol (100 ml) and 2N aqueous sodium hydroxide (49.8 ml) were added and stirred at 60 C. for 30 minutes. The mixture was concentrated under reduced pressure and acidified with 5N aqueous hydrochloric acid. The precipitate was filtrated, washed with water, dried and then recrystallized with ethanol to obtain 4.62 g of the title compound (CAS No. 13452-14-7). The structure of the obtained title compound and results from NMR measurement were as follows. 1H NMR (CD3OD) δ (ppm): 2.67 (3H, s), 7.67 (1H, d, J=8 Hz), 8.05 (1H, dd, J=1+8 Hz), 8.19 (1H, d, J=1 Hz).
 

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