Hydrogen Peroxide → HCID 21076085, compound

HRID 1374456Notes

Reaction equation

HRID 1374456 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][N:9]=[C:8](C(O)=O)[CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C(C1C=CN=CC=1)CCCC.[OH:26]O>C(O)(=O)C.C(Cl)Cl>[CH2:1]([C:6]1[CH:11]=[CH:10][N+:9]([O-:26])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 729184-PentylpyridineHCID 21076084HCID 21076084, compound

Product 1

HCID 21076085HCID 21076085, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

4-Pentylpyridine-2-carboxylic acid (10b) (R9=pentyl) was made by employing general Method P. To 4-pentylpyridine (3 g, 20 mmol) in acetic acid (30 mL), hydrogen peroxide (0.7 g, 30%, 20 mmol) was added and refluxed overnight. Removal of solvent resulted in residue which was dissolved in DCM (100 mL) dried over MgSO4 and filtered. Removal of DCM resulted in a brown liquid, 4-pentylpyridine-N-oxide, (3.3 g, 100%). To trimethylsilyl cyanide (2.37 g, 24 mmol), 4-pentylpyridine N-oxide (3.3 g, 20 mmol) in DCM (10 mL) was added followed by dropwise addition of dimethylcarbamoyl chloride (2.56 g, 24 mmol) in DCM (10 mL). After stirring at room temperature overnight, sodium bicarbonate (100 mL, 10%) was added and the organic layer was separated. The aqueous layer was extracted twice with DCM (50 mL) and the combined organic layer was dried over magnesium sulfate. Removal of solvent resulted in compound 10a (R9=pentyl) (4.1 g, 100%).

Workup

  1. temperaturerefluxed overnight
  2. customRemoval of solvent
  3. customresulted in residue which
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customRemoval of DCM

Sources & evidence

ORD record
ord-cd9a2ffc478c4fd99a81c6152ae87348
Source dataset
uspto-grants-2007_01
Patent number
US07164011B2

Reaction notes

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