Selenium Dioxide → HCID 25228377, compound

HRID 1920677Notes

Reaction equation

HRID 1920677 reaction equation
[Se](=O)=[O:2].[CH3:4][O:5][CH2:6][O:7][C:8]1[C:17]([C:18]#[N:19])=[C:16]2[C:11]([CH:12]=[CH:13][C:14]([CH3:20])=[N:15]2)=[CH:10][CH:9]=1>C1(C)C=CC=C(C)C=1>[CH:20]([C:14]1[CH:13]=[CH:12][C:11]2[C:16](=[C:17]([C:18]#[N:19])[C:8]([O:7][CH2:6][O:5][CH3:4])=[CH:9][CH:10]=2)[N:15]=1)=[O:2]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 25228375HCID 25228375, compound

Product 1

HCID 25228377HCID 25228377, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 7929M-XyleneSolvent

Conditions

Temperature
74 °C

Procedure

Referring to FIG. 20, under a nitrogen atmosphere selenium dioxide (0.0145 g, 0.131 mmol) was added to a solution of 8b (0.0300 g, 0.136 mmol) in m-xylene (5 mL). The mixture was stirred at 74° C. for 20 h then filtered. The filtrate was evaporated, and the residue was purified by column chromatography (3:7 EtOAc/hexane) to yield 9b (0.0100 g, 0.041 mmol, 30%) as a white solid: 1H NMR (CDCl3) δ 10.29 (1H, s), 8.34 (1H, d, J=8.0 Hz), 8.09 (1H, d, J=9.6 Hz), 8.04 (1H, d, J=8.0 Hz), 7.73 (1H, d, J=9.2 Hz), 5.50 (2H, s), 3.61 (3H, s); 13C NMR (CDCl3) δ 193.7, 163.0, 154.2, 148.6, 137.9, 133.9, 125.4, 118.5, 117.3, 114.3, 95.4, 57.3; FTIR (neat) 2922, 2846, 2224, 1710, 1260, 1165, 1043, 922, 856, 775 cm−1; MS (ESI) m/z calculated for (C13H10N2O3+H)+ 243, found 243; HRMS (ESI) m/z calculated for (C13H10N2O3+H)+ 243.0769, found 243.0764.

Workup

  1. filtrationthen filtered
  2. customThe filtrate was evaporated
  3. customthe residue was purified by column chromatography (3:7 EtOAc/hexane)

Sources & evidence

ORD record
ord-cdd6bae0cbc1410ba986a63907ac9f3f
Source dataset
uspto-grants-2012_05
Patent number
US08173620B2

Reaction notes

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