Methanol → Methyl 2-aminopyridine-4-carboxylate

HRID 985411

Reaction equation

HRID 985411 reaction equation
C([NH:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][N:13]=1)[C:8]([OH:10])=[O:9])(=O)C.[CH3:14]O>>[CH3:14][O:10][C:8](=[O:9])[C:7]1[CH:11]=[CH:12][N:13]=[C:5]([NH2:4])[CH:6]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 37744662-Acetamidopyridine-4-carboxylic acid

Product 1

HCID 236984Methyl 2-aminopyridine-4-carboxylate

Procedure

2-Acetylamino-isonicotinic acid (3.10 g, 17.2 mmol) was stirred in 35 mL MeOH at 0° C. HCl (g) was bubbled through the solution for 10 minutes and then the reaction was heated to reflux. After 16 hours the reaction was concentrated in vacuo. The residue was diluted with water and the pH was adjusted to 7 with Na2CO3 (s). A white precipitate formed which was filtered to afford a portion of pure desired product. The aqueous phase was extracted three times with 95:5 dichloromethane (DCM)/nBuOH. The organic phases were dried over Na2SO4, filtered and concentrated to afford more of the pure product as a white solid. 1H NMR (CDCl3) δ 8.19 (d, 1H, J=5.3 Hz), 7.17 (dd, 1H, J=1.4, 5.3 Hz), 7.07 (d, 1H, J=1.3 Hz), 4.64 (bs, 2H), 3.92 (s, 3H). MS [M+H]+=153.0.

Workup

  1. customHCl (g) was bubbled through the solution for 10 minutes
  2. temperaturethe reaction was heated to reflux
  3. concentrationAfter 16 hours the reaction was concentrated in vacuo
  4. additionThe residue was diluted with water
  5. customA white precipitate formed which
  6. filtrationwas filtered

Sources & evidence

ORD record
ord-567cb77995cb46e2af06a38391e05466
Source dataset
uspto-grants-2005_03
Patent number
US06872724B2

Linked notes

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