Selenium Dioxide → HCID 9817870, compound

HRID 396245Notes

Reaction equation

HRID 396245 reaction equation
[O:1]=[C:2]1[C:10]2([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:16]3[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=3)[CH:19]=[N:20]O)[CH:8]=2)[NH:3]1.[Se](=O)=O>C(Cl)(Cl)Cl>[O:1]=[C:2]1[C:10]2([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:16]3[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=3)[C:19]#[N:20])[CH:8]=2)[NH:3]1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 86585404HCID 86585404, compound

Product 1

HCID 9817870HCID 9817870, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 3-(1′,2′-Dihydro-2′-oxospiro[cyclohexane-1,3′-[3H]indol]-5′-yl)benzaldehyde oxime (0.48 g, 1.49 mmol) in chloroform (10 cm3) was treated with selenium dioxide (0.38 g, 3.50 mmol) and heated under reflux. After 16 h, the mixture was concentrated and the residue purified by column chromatography (SiO2,EtOAc: hexane 1:4) and the product re-crystallized from EtOAc-hexane to afford the title compound (0.161 g, 0.53 mmol, 35%) as a white solid: mp. 190-191° C.; 1H NMR (CDCl3) δ 1.59-1.87 (m, 6H), 1.88-2.09 (m, 4H), 7.03 (d, 1H, J=8 Hz), 7.42 (dd, 1H, J=8, 2 Hz), 7.54 (t, 1H, J=8 Hz), 7.58-7.65 (m, 2H), 7.78 (dt, 1H, J=7,2 Hz), 7.83 (m, 1H), 8.26 (s, 1H, br); MS ((+) ESI) m/z 303 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. concentrationthe mixture was concentrated
  4. customthe residue purified by column chromatography (SiO2,EtOAc: hexane 1:4)
  5. customthe product re-crystallized from EtOAc-hexane

Sources & evidence

ORD record
ord-0e08ea9be2474ae5923c6366687d62c3
Source dataset
uspto-grants-2003_08
Patent number
US06608068B2

Reaction notes

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