Ethanol → Ethyl 2-(5-aminopyridin-2-yl)acetate

HRID 2077774Notes

Reaction equation

HRID 2077774 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[N:6][CH:7]=1.OS(O)(=O)=O.C([O-])(O)=O.[Na+].[CH2:22](O)[CH3:23]>>[CH2:22]([O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([NH2:1])=[CH:7][N:6]=1)[CH3:23]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 218763062-(5-Aminopyridin-2-yl)acetic acid

Product 1

HCID 21876034Ethyl 2-(5-aminopyridin-2-yl)acetate

Procedure

To a solution of (5-amino-2-pyridinyl)acetic acid (1.46 g, 9.6 mmol, Daisley; R. W.; Hanbali, J. R., Synthetic Communications., 1981, 11(9), 743.) in ethanol was added conc. H2SO4 and stirred for 16.5 h under hydrogen atmosphere at room temperature. The mixture was neutralized with saturated NaHCO3 aqueous solution and the solvent was removed. The mixture was diluted with water and extracted with ethyl acetate (5×20 ml). The organic layer was washed with brine, dried (MgSO4) and concentrated to give 1.2 g of title compound as brown oil.

Workup

  1. customthe solvent was removed
  2. additionThe mixture was diluted with water
  3. extractionextracted with ethyl acetate (5×20 ml)
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b1c37eccf9a3481bb94bf88906c902fe
Source dataset
uspto-grants-2011_04
Patent number
US07928119B2

Reaction notes

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