Acetic Acid → Methyl 5-(2-cyanoethyl)-6-methoxynicotinate

HRID 709828Notes

Reaction equation

HRID 709828 reaction equation
[C:1]([CH:3]=[CH:4][C:5]1[C:6]([O:15][CH3:16])=[N:7][CH:8]=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11])#[N:2].C(O)(=O)C>[C].[Pd].CO>[C:1]([CH2:3][CH2:4][C:5]1[C:6]([O:15][CH3:16])=[N:7][CH:8]=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11])#[N:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 131733921HCID 131733921, compound

Product 1

HCID 117760240Methyl 5-(2-cyanoethyl)-6-methoxynicotinateYield 57.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of methyl 5-(2-cyanovinyl)-6-methoxynicotinate (1.02 g), acetic acid (20 ml) and methanol (20 mL) was added 10% palladium-carbon (504 mg), and the mixture was stirred under a hydrogen atmosphere at 70° C. for 40 hr. The reaction mixture was filtered, and the filtrate was diluted with THF and ethyl acetate. The diluted solution was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (589 mg) as white crystals.

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionthe filtrate was diluted with THF and ethyl acetate
  3. washThe diluted solution was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a8d13925a1ac4c3b813bbbe0895189ba
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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