6-Aminonicotinic acid → Methyl 6-aminonicotinate

HRID 1442783Notes

Reaction equation

HRID 1442783 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.Cl.[CH3:12]O>>[CH3:12][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([NH2:1])=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 184966-Aminonicotinic acidHCID 21893726Hydrochloride methanol

Product 1

HCID 737487Methyl 6-aminonicotinateYield 97%

Procedure

A solution of 6-aminonicotinic acid (3.0 g, 19 mmol) in HCl/MeOH (2M, 100 mL) was heated at reflux overnight. The solvent was removed under vacuum, and the residue was dissolved in ethyl acetate (200 mL) and washed with aqueous Na2CO3 solution and brine. The organic layer was dried over anhydrous Na2SO4 and concentrated to dryness to give 6-aminonicotinic acid methyl ester as a white solid (2.8 g, 97%), which was directly used in the next step without further purification. 1H NMR (300 MHz, d-DMSO) δ 8.48 (d, J=1.5 Hz, 1 H), 7.79 (dd, J=1.8, 6.6 Hz, 1H), 6.81 (brs, 2H), 6.42 (d, J=6.6 Hz, 1H), 3.73 (s, 3H).

Workup

  1. temperatureat reflux overnight
  2. customThe solvent was removed under vacuum
  3. dissolutionthe residue was dissolved in ethyl acetate (200 mL)
  4. washwashed with aqueous Na2CO3 solution and brine
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-208e670e07f044809569225857e8d49f
Source dataset
uspto-grants-2010_02
Patent number
US07659268B2

Reaction notes

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