Water → Methyl 5-isobutoxynicotinate

HRID 709759Notes

Reaction equation

HRID 709759 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH2:12](Br)[CH:13]([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:12]([O:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8])[CH:13]([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 354317Methyl 5-hydroxypyridine-3-carboxylate

Product 1

HCID 117760041Methyl 5-isobutoxynicotinate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Under a nitrogen atmosphere, to a solution of methyl 5-hydroxynicotinate (5.00 g) in DMF (50 mL) were added isobutyl bromide (5.33 mL) and potassium carbonate (9.04 g), and the mixture was stirred at 80° C. for 2 hr. Water was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. After silica gel filtration, the solvent was evaporated under reduced pressure to give a crude product of the title compound (5.13 g) as a pale-brown oil. The obtained crude product was directly used for the next step.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter silica gel filtration
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c1f953ee49e7433da0a0a76540785fc8
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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