Ozone → HCID 22419119, compound

HRID 1198724Notes

Reaction equation

HRID 1198724 reaction equation
[O:1]=[O+][O-].[CH3:4][O:5][C:6]1C=C[CH:9]=[C:10]2[C:15]=1[N:14]=[CH:13][C:12]([CH2:16][O:17][CH3:18])=[CH:11]2.C(#N)C.[OH2:22]>>[CH:9]([C:10]1[C:15]([C:6]([O:5][CH3:4])=[O:1])=[N:14][CH:13]=[C:12]([CH2:16][O:17][CH3:18])[CH:11]=1)=[O:22]

Participants

4

Reactant 3

HCID 24823OzoneHCID 18373917Acetonitrile--water (1/1)HCID 22419123HCID 22419123, compound

Product 1

HCID 22419119HCID 22419119, compound

Procedure

Ozone is bubbled through a solution of 8-methoxy-3-(methoxymethyl)quinoline (0.134 g, 0.66 mmol) in a 9:1 acetonitrile/water mixture at 0° C. After 10 minutes, the reaction mixture is concentrated in vacuo and the resulting oil is dissolved in methanol and treated with excess diazomethane. After stirring for 14 hours at room temperature, the reaction mixture is treated with acetic acid and concentrated in vacuo to obtain a red oil. Flash chromatography of the oil using silica gel and a 3:1 hexanes/ethyl acetate mixture gives the title product as a colorless oil which is identified by 1HNMR spectral analysis.

Workup

  1. concentrationthe reaction mixture is concentrated in vacuo
  2. dissolutionthe resulting oil is dissolved in methanol
  3. additiontreated with excess diazomethane
  4. additionthe reaction mixture is treated with acetic acid
  5. concentrationconcentrated in vacuo
  6. customto obtain a red oil

Sources & evidence

ORD record
ord-cf12cae09ba04c09984b0aa3b5e365c5
Source dataset
uspto-grants-1994_01
Patent number
US05281713

Reaction notes

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