Methanol → 5-Bromopyridine-2-carbaldehyde oxime

HRID 459012Notes

Reaction equation

HRID 459012 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=O)=[N:6][CH:7]=1.CO.Cl.[NH2:13][OH:14].C(=O)([O-])[O-].[Na+].[Na+]>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[N:13][OH:14])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 98775625-Bromopyridine-2-carbaldehyde

Product 1

HCID 1363756105-Bromopyridine-2-carbaldehyde oximeYield 92.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

5-Bromo-pyridine-2-carbaldehyde (X. Wang et al, Tetrahedron Letters 41 (2000), 4335–4338) (60 g, 322 mmol) was added to methanol (700 ml) and then water was added (700 ml) followed by addition of hydroxylamine hydrochloride (28 g, 403 mmol). Sodium carbonate (20.5 g, 193.2 mmol) in water (200 ml) was added and the reaction was stirred for 30 minutes. Water (500 ml) was then added and the precipitate was filtered and washed with water (2×300 ml) to give the desired product (60 g).

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with water (2×300 ml)

Sources & evidence

ORD record
ord-02ae2e7c912a4ea0b6b36934eeeed5ec
Source dataset
uspto-grants-2007_03
Patent number
US07192974B2

Reaction notes

Loading…