Ethanol → Ethyl 6-Aminonicotinate

HRID 8945

Reaction equation

HRID 8945 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[CH3:11][CH2:12]O>S(=O)(=O)(O)O>[CH2:11]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([NH2:1])=[N:3][CH:4]=1)[CH3:12]

Participants

4

Reactant 2

HCID 702EthanolHCID 184966-Aminonicotinic acid

Product 1

HCID 235927Ethyl 6-AminonicotinateYield 92%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 6-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 6-aminonicotinic acid ethyl ester (2.18 g, 92%) as a white powder. 1H NMR (CDCl3) δ 1.37 (t, 3H, J=6.0 Hz), 4.34 (q, 2H, J=7.0 Hz), 4.89 (br s, 2H (NH2)), 6.46 (d, 1H, J=7.5 Hz), 8.02 (d, 1H, J=7.5 Hz), 8.73 (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-f9221e72fbe144d09bdbb0a053ea0eea
Source dataset
uspto-grants-2006_08
Patent number
US07091217B2

Linked notes

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