Pyridine → HCID 178526384, compound

HRID 1596809Notes

Reaction equation

HRID 1596809 reaction equation
Cl.[C:2]([NH:6][OH:7])(C)(C)[CH3:3].N1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[C:3]1([CH:2]=[NH+:6][O-:7])[C:12]2[C:11]([CH:12]=[CH:13][CH:9]=[CH:10][CH:11]=2)=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 1049PyridineHCID 2777896N-tert-butylhydroxylamine hydrochloride

Product 1

HCID 178526384HCID 178526384, compoundYield 96%

Conditions

Temperature
95 °C

Procedure

A carboxaldehyde group is converted readily to, for example, a N-tert-butyl nitrone group, by the following method: To a 0.2M solution of the aldehyde obtained by Procedure B in dry pyridine under argon at rt is added solid N-tert-butylhydroxylamine hydrochloride (1.5-2.0 eq). The mixture is heated with stirring to 95° C. for one hour and then allowed to cool to rt. The pyridine is removed on the rotary evaporator, and the residue is dissolved in CDCl3. The CDCl3 layer is washed with water and dried over MgSO4. Evaporation of the CDCl3 followed by silica gel chromatography of the residue (CDCl3:MeOH) provides the solid green azulenyl nitrone in 96% yield.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto cool to rt
  3. customThe pyridine is removed on the rotary evaporator
  4. dissolutionthe residue is dissolved in CDCl3
  5. washThe CDCl3 layer is washed with water
  6. dry with materialdried over MgSO4
  7. customEvaporation of the CDCl3

Sources & evidence

ORD record
ord-70050413958647bf8cea27d5fdcacab7
Source dataset
uspto-grants-2001_09
Patent number
US06291702B1

Reaction notes

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