2-Propenyl-6-methylisonicotinic acid ethyl ester → 2-Propyl-6-methylisonicotinic acid ethyl ester

HRID 1908716Notes

Reaction equation

HRID 1908716 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]([CH:12]=[CH:13][CH3:14])[CH:6]=1)[CH3:2]>C1COCC1.[Pd]>[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]([CH2:12][CH2:13][CH3:14])[CH:6]=1)[CH3:2]

Participants

4

Reactant 1

HCID 670271022-Propenyl-6-methylisonicotinic acid ethyl ester

Product 1

HCID 669335582-Propyl-6-methylisonicotinic acid ethyl esterYield 101.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-propenyl-6-methylisonicotinic acid ethyl ester (2.25 g, 10.9 mmol) is dissolved in THF (100 mL), Pd/C (300 mg, 10% Pd) is added and the mixture is stirred under 1 atm H2 at rt for 15 h. The catalyst is filtered off and the filtrate is evaporated to give 2-propyl-6-methylisonicotinic acid ethyl ester (2.30 g) as a colourless oil; LC-MS: tR=0.65 min, [M+1]+=208.12.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-9c779ed4486f468a8d07b65709161eba
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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