6-Bromopyridine-2-carbaldehyde → 6-bromopyridine-2-carbaldehyde O-(2-hydroxy-2-methylpropyl)oxime

HRID 386121Notes

Reaction equation

HRID 386121 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]=O)[CH:5]=[CH:4][CH:3]=1.Cl.[NH2:11][O:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15]>C(O)C.C(OCC)(=O)C>[OH:16][C:14]([CH3:17])([CH3:15])[CH2:13][O:12][N:11]=[CH:8][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=1

Participants

5

Reactant 2

HCID 27570096-Bromopyridine-2-carbaldehydeHCID 231323651-(Aminooxy)-2-methylpropan-2-ol hydrochloride

Product 1

HCID 866462866-bromopyridine-2-carbaldehyde O-(2-hydroxy-2-methylpropyl)oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-bromopyridine-2-carbaldehyde (334 mg, 1.80 mmol) and 1-(aminooxy)-2-methylpropan-2-ol hydrochloride salt (254.6 mg, 1.80 mmol) were stirred in ethanol (5 ml) for one hour at 10° C. The reaction mixture was cooled to room temperature and diluted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Column chromatography from 100% hexanes to 30% ethyl acetate afforded the title compound as E/Z mixture.

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a97deab2865842c3bf18d98b09f58e49
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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