Ethanol → HCID 178510832, compound

HRID 1891835Notes

Reaction equation

HRID 1891835 reaction equation
C(O)C.[CH2:4]([O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][C:19]#[N:20])=[N:16][CH:17]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl-].[OH:22][NH3+:23].C(=O)([O-])[O-].[K+].[K+]>O>[CH2:4]([O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][C:19]([NH:23][OH:22])=[NH:20])=[N:16][CH:17]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 21645Hydroxylamine HClHCID 221813855-Benzyloxy-2-cyanomethylpyridine

Product 1

HCID 178510832HCID 178510832, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To an ethanol (30 mL) solution of (5-benzyloxy-pyridin-2-yl)-acetonitrile (1.77 g, 7.89 mmol) described in Manufacturing Example 127-1-4 were added hydroxylammonium chloride (848 mg, 11.8 mmol) and potassium carbonate (2.18 g, 15.8 mmol), which was stirred for 11 hours and 20 minutes at 70° C. The mixture was then stirred for another 5 hours and 45 minutes under reflux. Water was added to the reaction mixture at room temperature, which was extracted with ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:1) to obtain the title compound (550 mg, 27%).

Workup

  1. stirringThe mixture was then stirred for another 5 hours and 45 minutes
  2. temperatureunder reflux
  3. extractionwhich was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:1)

Sources & evidence

ORD record
ord-cd93b34ee7f0442fbd70236e65092a0d
Source dataset
uspto-grants-2013_08
Patent number
US08507530B2

Reaction notes

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