Triethylamine → 3-Methoxypyrazine-2-carboxaldehyde oxime

HRID 2105239Notes

Reaction equation

HRID 2105239 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH:9]=O)=[N:5][CH:6]=[CH:7][N:8]=1.Cl.[NH2:12][OH:13].C(N(CC)CC)C>C(O)C>[CH3:1][O:2][C:3]1[C:4]([CH:9]=[N:12][OH:13])=[N:5][CH:6]=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 158805973-Methoxypyrazine-2-carbaldehyde

Product 1

HCID 1364153973-Methoxypyrazine-2-carboxaldehyde oximeYield 32.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-methoxypyrazine-2-carboxaldehyde (Tetrahedron (1999), 56(2), 265-273) (2.1 g, 15 mmol), hydroxylamine hydrochloride (1.27 g, 18 mmol), ethanol (20 ml) and triethylamine (4.17 ml, 30 mmol) was heated at 60° C. for 90 minutes. The volatiles were removed by evaporation and residue was purified by column chromatography on silica gel eluting with hexane/EtOAc (100:0 increasing in polarity 0:100) to give the title compound (740 mg, 32%) as a white solid.

Workup

  1. customThe volatiles were removed by evaporation and residue
  2. customwas purified by column chromatography on silica gel eluting with hexane/EtOAc (100:0 increasing in polarity 0:100)

Sources & evidence

ORD record
ord-2286b710b55f4e08b5c1ace1b51e54e0
Source dataset
uspto-grants-2009_08
Patent number
US07579349B2

Reaction notes

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