Methanol → Methyl 2-(6-aminopyridin-3-yl)-2-methylpropanoate

HRID 377221Notes

Reaction equation

HRID 377221 reaction equation
Cl.[NH2:2][C:3]1[N:8]=[CH:7][C:6]([C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.OS(O)(=O)=O.[CH3:20]O>>[NH2:2][C:3]1[N:8]=[CH:7][C:6]([C:9]([CH3:14])([CH3:13])[C:10]([O:12][CH3:20])=[O:11])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 671308492-(6-Aminopyridin-3-yl)-2-methylpropanoic acid hydrochloride

Product 1

HCID 21998700Methyl 2-(6-aminopyridin-3-yl)-2-methylpropanoate

Procedure

A solution of 2-(6-aminopyridin-3-yl)-2-methylpropanoic acid hydrochloride (35.0 g, 0.162 mmol) and concentrated H2SO4 (5 mL) in MeOH (250 mL) was heated at reflux overnight. After cooling to ambient temperature, the reaction was quenched cautiously with saturated aqueous NaHCO3 and concentrated in vacuo. The residue was partitioned between ethyl acetate and water, the organic phase separated and the aqueous phase re-extracted with ethyl acetate (.Yen.3). The combined organic extract was washed with brine, dried (MgSO4) and concentrated in vacuo. The residue (31.6 g, 100%) was judged pure by a combination of TLC and 1H nmr analysis and was used without further purification in the subsequent reaction.

Workup

  1. temperatureat reflux overnight
  2. customthe reaction was quenched cautiously with saturated aqueous NaHCO3
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between ethyl acetate and water
  5. customthe organic phase separated
  6. extractionthe aqueous phase re-extracted with ethyl acetate (.Yen.3)
  7. extractionThe combined organic extract
  8. washwas washed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated in vacuo
  11. customwas used without further purification in the subsequent reaction

Sources & evidence

ORD record
ord-3465bd294fce4eaca68cb7e49179caa4
Source dataset
uspto-grants-2000_02
Patent number
US06025366

Reaction notes

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