Potassium Carbonate → (E)-N-methoxy-1-[5-(2-phenylethynyl)-3-pyridinyl]methanimine;hydrochloride

HRID 606832Notes

Reaction equation

HRID 606832 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[C:11]([CH:15]=O)[CH:12]=[N:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[ClH:23].[O:24]([NH2:26])[CH3:25]>C(O)C>[ClH:23].[CH3:25][O:24]/[N:26]=[CH:15]/[C:11]1[CH:12]=[N:13][CH:14]=[C:9]([C:8]#[C:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 10679834HCID 10679834, compound

Product 1

HCID 87248550(E)-N-methoxy-1-[5-(2-phenylethynyl)-3-pyridinyl]methanimine;hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve 5-phenylethynylpyridine-3-carbaldehyde (0.20 g, 0.97 mmol), (prepared essentially as described in EXAMPLE 5), in ethanol (2.0 mL) and sequentially add potassium carbonate (0.67 g, 4.8 mmol) and methoxylamine hydrochloride (0.64 g, 5.6 mmol). Heat at reflux overnight, cool to room temperature and filter. Concentrate and purify by silica gel chromatography, eluting with a linear gradient of 90:10 to 50:50 hexanes:ethyl acetate to obtain the free base of the title compound as a colorless oil as well as a minor amount of EXAMPLE 86.

Workup

  1. custom(prepared essentially
  2. temperatureHeat
  3. temperatureat reflux overnight
  4. filtrationfilter
  5. concentrationConcentrate
  6. custompurify by silica gel chromatography
  7. washeluting with a linear gradient of 90:10 to 50:50 hexanes

Sources & evidence

ORD record
ord-22b06b09a20e45aca86dc4cccc5c7285
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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