Selenium Dioxide → HCID 86639217, compound

HRID 1920682Notes

Reaction equation

HRID 1920682 reaction equation
[Se](=O)=O.[Cl:4][C:5]1[C:6]([CH2:15][O:16][CH3:17])=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][CH:11]=[CH:10]2.[O:18]1CCOC[CH2:19]1>>[Cl:4][C:5]1[C:6]([CH2:15][O:16][CH3:17])=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[C:12]([CH:19]=[O:18])[CH:11]=[CH:10]2

Participants

4

Reactant 3

HCID 24007Selenium DioxideHCID 312751,4-DioxaneHCID 674918338-Chloro-7-methoxymethylquinoline

Product 1

HCID 86639217HCID 86639217, compoundYield 56%

Conditions

Temperature
85 °C

Procedure

Referring to FIG. 20, under a nitrogen atmosphere, selenium dioxide (0.0604 g, 0.544 mmol) was added to a solution of 8c (0.1232 g, 0.5184 mmol) in p-dioxane (3 mL), and the resulting orange solution was stirred in a sealed flask for 2 h at 85° C. The black precipitate was removed by vacuum filtration and the filtrand was evaporated, leaving a residue, which was purified by column chromatography (2:8 EtOAc/hexane) to afford 9c (0.0724 g, 0.288 mmol, 56%) as a pale yellow solid (mp 118-121° C.): 1H NMR (CDCl3) δ 10.30 (1H, s), 8.30 (1H, d, J=8.0 Hz), 7.99, (1H, d, J=8.0 Hz), 7.81 (1H, d, J=9.6 Hz), 7.70 (1H, d, J=8.8 Hz), 5.45 (2H, s), 3.60 (3H, s); 13C NMR (CDCl3) δ 193.9, 154.7, 153.4, 145.6, 138.0, 127.2, 127.0, 121.3, 120.2, 116.5, 95.7, 57.0; FTIR (neat) 2931, 2835, 1713, 1615, 1303, 1159, 1043, 920, 775 cm−1; MS (ESI) m/z calculated for (C12H10ClNO3+H)+ 252 (35Cl) and 254 (37Cl), found 252 (35Cl) and 254 (37Cl); HRMS (ESI) m/z calculated for (C12H10ClNO3+H)+ 252.0427 (35Cl) and 254.0398 (37Cl), found 252.0418 (35Cl) and 254.0390 (37Cl).

Workup

  1. customThe black precipitate was removed by vacuum filtration
  2. customthe filtrand was evaporated
  3. customleaving a residue, which
  4. customwas purified by column chromatography (2:8 EtOAc/hexane)

Sources & evidence

ORD record
ord-6067fe88a8374746aa67d989aeee82ba
Source dataset
uspto-grants-2012_05
Patent number
US08173620B2

Reaction notes

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