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Structure of 884306-77-8

Chemical Structure| 884306-77-8

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Product Details of [ 884306-77-8 ]

CAS No. :884306-77-8
Formula : C13H15NO4
M.W : 249.26
SMILES Code : O=C(OCC1=CC=CC=C1)NC(C2)COCC2=O
MDL No. :MFCD29053006

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Application In Synthesis of [ 884306-77-8 ]

* 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 [ 884306-77-8 ]

[ 884306-77-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 884306-77-8 ]
  • [ 14150-94-8 ]
  • [ 884306-78-9 ]
  • [ 884306-79-0 ]
YieldReaction ConditionsOperation in experiment
With ammonia; In methanol; at 120℃; for 0.333333h;Irradiation; 31.2 Benzyl 3,4-dihydro-7-nitro-2H-pyrano[3,2-b]pyridin-3-ylcarbamate and hon-7.,. beta R-HihvHm-'i-nitrn-fiH-nvrannR 4-blnvridin-5-vlcarbamate ; EPO <DP n="119"/>A solution of (delta-oxo-tetrahydro-pyran-S-yO-carbamic acid benzyl ester (750 mg, 3 mmol) and 1-methyl-3,5-dinitro-2-pyridone (660 g, 3.31 mmol) in methanolic am¬ monia (1 M, 6 ml) was irradiated in a sealed vial at 12O0C for 20 min. The mixture was then concentrated and the resulting residue was dissolved in CH2CI2. The organic layer was washed with saturated aqueous NaHCO3 and water, dried over Na2SO4 and evaporated. Purification of the resulting residue by chromatography on silica gel (heptane:ethyl acetate, 3:1) afforded a mixture 7.5/1 (632 mg, 64%) of benzyl 6,8-dihydro-3-nitro-5H-pyrano[3,4-b]pyridin-5-ylcarbamate as major product along with benzyl 3,4-dihydro-7-nitro-2H-pyrano[3,2-b]pyridin-3- ylcarbamate as minor adduct. A small fraction of each was isolated to afford full characterization.Benzyl 3,4-dihydro-7-nitro-2H-pyrano[3,2-b]pyridin-3-yl-carbamate: white solid MS (ESI+) m/z = 330.1 [M+H]+.1H NMR (400 MHz, CDCI3) delta 3.10 (dd, J = 18.1 , 3.5 Hz1 1H), 3.34 (dd, J = 18.2,5.3 Hz, 1H), 4.25 (s, 2H), 4.39 (br s, 1H), 5.02 (br s, 1H), 5.10 (s, 2H), 7.33 (m,5H), 7.90 (d, J = 2.0 Hz, 1H), 8.98 (d, J = 2.0 Hz, 1H);13C NMR (100 MHz, CDCI3) 534.9, 43.7, 67.2, 68.7, 118.6, 128.2 (2C), 128.3, 128.5 (2C), 135.8, 137.2, 143.6, 148.0, 150.3, 155.4.Anal, calcd. for C16H15N3O5: C, 58.36; H, 4.59; N, 12.76; O, 24.29. Found: C,58.76; H, 5.00; N, 12.23; O, 24.12.Benzyl 6,8-dihydro-3-nitro-5H-pyrano[3,4-b]pyridin-5-yl-carbamate: light yellow solidMS (ESI+) m/z = 330.1 [M+H]+.1H NMR (400 MHz1 CDCI3) delta 3.96 (dd, J = 11.9, 3.2 Hz1 1 H), 4.07 (dd, J = 11.9,2.9 Hz1 1 H)1 4.80 (d, J = 17.4 Hz1 1H)1 4.94 (d, J = 17.4 Hz, 1H), 5.00 (m, 1 H),5.13 (d, J = 12.3 Hz, 1H), 5.17 (d, J = 12.3 Hz, 1H), 5.38 (d, J = 9.0 Hz, 1H), 7.35 (m, 5H), 8.61 (d, J = 1.6 Hz1 1 H), 9.29 (d, J = 1.9 Hz, 1 H);13C NMR (100 MHz, CDCI3) 546.7, 67.3, 68.8, 69.8, 128.1 (2C), 128.3, 128.5(2C)1 130.9, 131.8, 135.8, 143.2, 144.1, 155.8, 160.8;Anal, calcd for C16H15N3O5: C, 58.36; H, 4.59; N, 12.76; O, 24.29. Found: C,58.46; H, 4.80; N, 12.59; O, 23.98.
 

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