Selenium Dioxide → HCID 25228494, compound

HRID 1920686Notes

Reaction equation

[CH3:1][N:2]([CH3:14])[C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([CH3:13])=[N:10]2)=[CH:5][CH:4]=1.[Se](=O)=[O:16]>>[CH3:1][N:2]([CH3:14])[C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([CH:13]=[O:16])=[N:10]2)=[CH:5][CH:4]=1

Participants

Reactant 2

HCID 24007Selenium Dioxide

HCID 326819HCID 326819, compound

Product 1

HCID 25228494HCID 25228494, compoundYield 42%

Conditions

Temperature: 90 °C

Procedure

Referring to FIG. 21, compound 13a (304.3 mg, 1.63 mmol) was dissolved in m-xylenes (2 mL) and stirred under a nitrogen atmosphere. Selenium dioxide (272.29 mg 2.45 mmol) was added and the yellow-orange mixture was heated to 90° C. for 4 h. The black reaction mixture was filtered through cotton, washing several times with chloroform. The filtrate was directly adsorbed onto silica gel and purified by column chromatography (EtOAc) to afford 14a (136.4 mg, 0.68 mmol, 42%) as a pale yellow oil: 1H NMR (CDCl3,) δ 10.11 (1H, s), 8.11 (1H, d, J=8.0 Hz), 7.74 (1H, d, J=8.4 Hz), 7.73 (1H, d, J=8.0 Hz), 7.31 (1H, dd, J=9.6, 2.8 Hz), 7.23 (1H, d, J=1.6 Hz), 3.15 (6H, s); 13C NMR (CDCl3,) δ 194.5, 153.0, 151.9, 150.2, 136.9, 128.6, 123.1, 119.1, 113.8, 107.0, 40.7; FTIR (neat) 2920, 1705, 1620, 1537, 1508, 1382, 1255, 1155, 1066, 835, 761 cm−1; MS (ESI) m/z calculated for (C12H12N2O+H)+ 201, found, 201; HRMS (ESI) m/z calculated for (C12H12N2O+H)+ 201.1028, found, 201.1055.

Workup

customThe black reaction mixture
filtrationwas filtered through cotton
washwashing several times with chloroform
custompurified by column chromatography (EtOAc)

Sources & evidence

ORD record: ord-e7535f45f4f74b6aa04f1fd9fd84e1fb
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173620B2

Reaction notes

Loading…