Hydroxyamine hydrochloride → 2-Amino-pyridine-3-carbaldehyde oxime

HRID 640138

Reaction equation

HRID 640138 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=O)=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.[NH2:11][OH:12]>N1C=CC=CC=1>[NH2:1][C:2]1[C:7]([CH:8]=[N:11][OH:12])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 7376333-Pyridinecarboxaldehyde, 2-amino-

Product 1

HCID 533951902-Amino-pyridine-3-carbaldehyde oximeYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-amino-3-formylpyridine (1.00 g, 8.19 mmol) in pyridine (20 mL) was added hydroxylamine hydrochloride (854 mg, 12.3 mmol) at room temperature, which was stirred for 1 hour and 40 minutes at room temperature. The reaction solution was partitioned into water and ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=10:1) to obtain the title compound (951 mg, 85%).

Workup

  1. customThe reaction solution was partitioned into water and ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under a reduced pressure
  5. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=10:1)

Sources & evidence

ORD record
ord-f6761e9ab0894d0ba8cc546ca64cdd86
Source dataset
uspto-grants-2010_04
Patent number
US07691882B2

Linked notes

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