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

HRID 77856

Reaction equation

HRID 77856 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-7d48683d5bce425bb760a1b931bcd747
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Linked notes

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