Methanol → Methyl 6-aminonicotinate

HRID 1670689Notes

Reaction equation

HRID 1670689 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.S(=O)(=O)(O)O.[CH3:16]O>>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([O:8][CH3:16])=[O:7])=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 184966-Aminonicotinic acid

Product 1

HCID 737487Methyl 6-aminonicotinateYield 64%

Procedure

A mixture of 6-aminonicotinic acid (1.0 equiv., 7.24 mmol, 1.00 g) and sulfuric acid (6.00 equiv., 65.16 mmol, 6.39 g) in methanol was refluxed for 24 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure and then made alkaline by the addition of a saturated aqueous NaHCO3 solution. The aqueous layer was extracted with ethyl acetate, the combined organic layers were dried with MgSO4 and concentrated in vacuo to give methyl 6-amino-pyridine-3-carboxylate (15) (0.70 g, yield=64%) as a white crystalline product.

Workup

  1. temperaturewas refluxed for 24 h
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionby the addition of a saturated aqueous NaHCO3 solution
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialthe combined organic layers were dried with MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-642c77aad3744e3da13cb676ebef32b8
Source dataset
uspto-grants-2011_08
Patent number
US07994187B2

Reaction notes

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