Hydrochloric Acid → 3-Methyl-2,3'-bipyridine

HRID 7326Notes

Reaction equation

HRID 7326 reaction equation
O[CH2:2][C:3]1[C:4]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[N:5][CH:6]=[CH:7][CH:8]=1.Cl.O1CCOCC1>[Pd].CO>[CH3:2][C:3]1[C:4]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 160370823-Hydroxymethyl-2,3'-bipyridyl

Product 1

HCID 160371763-Methyl-2,3'-bipyridineYield 76.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 3-hydroxymethyl-2,3′-bipyridyl (42.3 mg, 0.227 mmole) solution containing methanol (5 ml) and 4N solution of hydrogen chloride in dry 1,4-dioxane (0.57 ml, 2.3 mmole) was hydrogenated in the presence of palladium on activated carbon catalyst (10%, 40 mg) at room temperature and ambient pressure for 3 hours. The catalyst was filtered off, washed with methanol (3×1 ml), and the combined methanolic solutions were evaporated under vacuum. The residue was dissolved in water (2 ml), sodium carbonate was added (0.1 g) and the solution was extracted with dichloromethane (3×2 ml). The combined dichloromethane solutions were dried (magnesium sulfate) and rotary evaporated at 2 mm Hg-45° C., giving the pure product (29.4 mg, 76%) as a colorless oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with methanol (3×1 ml)
  3. customthe combined methanolic solutions were evaporated under vacuum
  4. dissolutionThe residue was dissolved in water (2 ml)
  5. additionsodium carbonate was added (0.1 g)
  6. extractionthe solution was extracted with dichloromethane (3×2 ml)
  7. dry with materialThe combined dichloromethane solutions were dried (magnesium sulfate)
  8. customrotary evaporated at 2 mm Hg-45° C.

Sources & evidence

ORD record
ord-522eee91ca144361b417e0fe45341314
Source dataset
uspto-grants-2006_08
Patent number
US07087106B2

Reaction notes

Loading…