6-Aminopyridine-2-carboxylic acid → 247100-92-1

HRID 2120070Notes

Reaction equation

HRID 2120070 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([OH:10])=[O:9])[N:3]=1.[ClH:11].O1CCO[CH2:14][CH2:13]1>CCO>[ClH:11].[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([O:10][CH2:13][CH3:14])=[O:9])[N:3]=1

Participants

4

Reactant 2

HCID 3516526-Aminopyridine-2-carboxylic acidHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 23437674247100-92-1

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 2-aminopyridine-6-carboxylic acid (2 g) in EtOH (10.0 mL) and 4N HCl/dioxane (10.0 mL) was heated to reflux for 16 hours under anhydrous conditions. The reaction mixture was then concentrated to dryness and the residue was dried in a desiccator under vacuum to afford 2-amino-6-carbethoxypyridine hydrochloride as a white powder (1.6 g). 1H-NMR (DMSO-d6) δ 8.3 (br), 7.94 (m, 1H), 7.37 (d, 1H, J=7.2 Hz), 7.22 (dd, 1H, J=8.7 Hz), 4.37 (q, 2H, J=7.2 Hz), 1.32 (t, 3H, J=7.2 Hz); FAB MS m/z 167 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 hours under anhydrous conditions
  3. concentrationThe reaction mixture was then concentrated to dryness
  4. customthe residue was dried in a desiccator under vacuum

Sources & evidence

ORD record
ord-58598f39fe024459a2e6ab0ed6047c8f
Source dataset
uspto-grants-2004_02
Patent number
US06689754B1

Reaction notes

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