Selenium Dioxide → HCID 9817870, compound

HRID 1264510Notes

Reaction equation

HRID 1264510 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-1569143875fe47cd9e1228765fed7649
Source dataset
uspto-grants-2003_04
Patent number
US06544970B2

Reaction notes

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