2-Methyl-6-(2-methylpropenyl)isonicotinic acid ethyl ester → 2-Methyl-6-(2-methyl-propyl)-isonicotinic acid ethyl ester

HRID 1908720Notes

Reaction equation

HRID 1908720 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[C:9]([CH:11]=[C:12]([CH3:14])[CH3:13])[N:8]=[C:7]([CH3:15])[CH:6]=1)[CH3:2]>C1COCC1.CO.[Pd]>[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[C:9]([CH2:11][CH:12]([CH3:13])[CH3:14])[N:8]=[C:7]([CH3:15])[CH:6]=1)[CH3:2]

Participants

5

Reactant 1

HCID 574371992-Methyl-6-(2-methylpropenyl)isonicotinic acid ethyl ester

Product 1

HCID 574372012-Methyl-6-(2-methyl-propyl)-isonicotinic acid ethyl esterYield 97.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Methyl-6-(2-methyl-propenyl)-isonicotinic acid ethyl ester (9.90 g, 45.2 mmol) is dissolved in THF (100 mL) and methanol (100 mL), Pd/C (800 mg, 10% Pd) is added and the mixture is stirred under 1 atm H2 at rt for 5 h. The catalyst is filtered off and the filtrate is evaporated. The crude product is purified by CC on silica gel eluting with hexane:EA 1:1 to give 2-methyl-6-(2-methyl-propyl)-isonicotinic acid ethyl ester (9.78 g) as a colourless oil; LC-MS: tR=0.71 min.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. customThe crude product is purified by CC on silica gel eluting with hexane:EA 1:1

Sources & evidence

ORD record
ord-2d0925b9615a41959c375f4324fea6f4
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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