Methyl 3-ethenylpyridine-2-carboxylate → Methyl 3-ethylpicolinate

HRID 1945345Notes

Reaction equation

HRID 1945345 reaction equation
[CH:1]([C:3]1[C:4]([C:9]([O:11][CH3:12])=[O:10])=[N:5][CH:6]=[CH:7][CH:8]=1)=[CH2:2]>[Pd].C(O)C>[CH2:1]([C:3]1[C:4]([C:9]([O:11][CH3:12])=[O:10])=[N:5][CH:6]=[CH:7][CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 15257081Methyl 3-ethenylpyridine-2-carboxylate

Product 1

HCID 40151854Methyl 3-ethylpicolinate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium on carbon (10%, 25 mg) was added to a solution of methyl 3-vinylpicolinate (120 mg, 0.74 mmol) in ethanol (10 mL). The suspension was stirred at room temperature under an atmosphere of hydrogen for 1 h before it was filtered through Celite and the pad of Celite was washed with methanol. The filtrate was concentrated down to dryness to yield methyl 3-ethylpicolinate (i.e. Cap-175, step b) which was taken directly into the next reaction. Rt=1.15 min (Cond.-MD1); LC/MS: Anal. Calcd. for [M+H]+ C9H12NO2: 166.09; found: 166.09.

Workup

  1. filtrationwas filtered through Celite
  2. washthe pad of Celite was washed with methanol
  3. concentrationThe filtrate was concentrated down to dryness

Sources & evidence

ORD record
ord-8e449f086f8148219c8cfe5a6b88e34f
Source dataset
uspto-grants-2013_03
Patent number
US08394968B2

Reaction notes

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