Ethanol → Ethyl 5-aminopyridine-2-carboxylate

HRID 2241166Notes

Reaction equation

HRID 2241166 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.S(=O)(=O)(O)O.C([O-])([O-])=O.[Na+].[Na+].[CH2:22](O)[CH3:23]>>[CH2:22]([O:9][C:8]([C:5]1[CH:4]=[CH:3][C:2]([NH2:1])=[CH:7][N:6]=1)=[O:10])[CH3:23]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 41797265-Aminopyridine-2-carboxylic acid

Product 1

HCID 13816714Ethyl 5-aminopyridine-2-carboxylateYield 89%

Conditions

Temperature
0 °C

Procedure

A solution of 5-amino-pyridine-2-carboxylic acid (1.0 g, 5.9 mmol) in ethanol (15.0 ml) was treated with concentrated sulfuric acid (0.30 ml) and stirred at reflux overnight. The mixture was cooled to 0° C. and treated with 1M Na2CO3 until pH 8 was reached (4.0 ml). A precipitate formed, which was filtered washing with ethanol/water 2:1, and dried under vacuum, yielding 5-amino-pyridine-2-carboxylic acid ethyl ester (1.03 g, 89%) as a white solid, MS (EI): m/e=196.0 (M+).

Workup

  1. temperatureat reflux overnight
  2. customA precipitate formed
  3. filtrationwhich was filtered
  4. washwashing with ethanol/water 2:1
  5. customdried under vacuum

Sources & evidence

ORD record
ord-5aca7d5af62c49fcbc0573e100926b62
Source dataset
uspto-grants-2010_05
Patent number
US07723538B2

Reaction notes

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