Ethanol → Ethyl 2-aminopyridine-3-carboxylate

HRID 1582285Notes

Reaction equation

HRID 1582285 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:11][CH2:12]O>S(=O)(=O)(O)O>[CH2:11]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[N:10][C:2]=1[NH2:1])[CH3:12]

Participants

4

Reactant 2

HCID 702EthanolHCID 729302-Aminonicotinic acid

Product 1

HCID 12433260Ethyl 2-aminopyridine-3-carboxylateYield 74%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2-aminonicotinic acid (2.0 g, 14.4 mmol) in anhydrous EtOH (70 mL) and concentrated sulfuric acid (14 mL) was heated to reflux for 16 h. The solution was concentrated under reduced pressure, neutralized with saturated aqueous Na2CO3 (50 mL) and extracted with CH2Cl2 (3×50 mL). The combined organic phases were dried (MgSO4), filtered and concentrated to give 2-aminonicotinic acid ethyl ester as a yellow solid (1.74 g, 74%). 1H NMR (CDCl3) δ1.40 (t, 3H, J=6.0 Hz), 4.34 (q, 2H, J=7.0 Hz), 6.41 (br s, 2H (NH2)), 6.63 (m, 1H), 8.14 (d, 1H, J=7.8 Hz), 8.22 (s, 1H).

Workup

  1. temperatureto reflux for 16 h
  2. concentrationThe solution was concentrated under reduced pressure
  3. extractionextracted with CH2Cl2 (3×50 mL)
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-05c0f700018f4ee99ad9a7f17cd4f693
Source dataset
uspto-grants-2004_05
Patent number
US06734191B2

Reaction notes

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