Methanol → Methyl 6-(ethylamino)pyridine-3-carboxylate

HRID 427747Notes

Reaction equation

HRID 427747 reaction equation
[CH2:1]([NH:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=1)[CH3:2].OS(O)(=O)=O.[CH3:18]O>>[CH2:1]([NH:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([O:10][CH3:18])=[O:9])=[CH:6][N:5]=1)[CH3:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 117449946-(Ethylamino)pyridine-3-carboxylic acid

Product 1

HCID 11126856Methyl 6-(ethylamino)pyridine-3-carboxylateYield 84%

Procedure

A suspension of 6-(ethylamino)nicotinic acid (50 g, 0.3 mol) in methanol (500 ml) was treated with concentrated H2SO4 (30 mml). The reaction was heated at reflux for 18 hours. The reaction mixture was then evaporated, poured into ice water (1 L) and adjusted to pH 8 with solid sodium hydrogen carbonate (foaming). The aqueous mixture was extracted with ethyl acetate (3×300 ml) and the organic layers combined, dried (MgSO4) and evaporated to give methyl 6-(ethylamino)nicotinoate as an off-white solid (45.5 g, 84%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 18 hours
  3. customThe reaction mixture was then evaporated
  4. additionpoured into ice water (1 L)
  5. extractionThe aqueous mixture was extracted with ethyl acetate (3×300 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-402de9e8ffee45aa8dc1872846c35589
Source dataset
uspto-grants-2001_11
Patent number
US06313148B1

Reaction notes

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