Sulfuric Acid → Methyl 6-aminopyridine-2-carboxylate

HRID 1809449Notes

Reaction equation

HRID 1809449 reaction equation
OS(O)(=O)=O.[NH2:6][C:7]1[N:12]=[C:11]([C:13]([OH:15])=[O:14])[CH:10]=[CH:9][CH:8]=1.[C:16]([O-])(O)=O.[Na+]>CO>[NH2:6][C:7]1[N:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 3516526-Aminopyridine-2-carboxylic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 13809143Methyl 6-aminopyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

H2SO4 (3.0 eq.) was added to a suspension of 6-aminopyridine-2-carboxylic acid in MeOH (0.3 M). The reaction mixture was heated to reflux for 20 h. After cooling down, the solvent was reduced in vacuo and the residue was added to cooled sat. aq. NaHCO3. The aqueous phase was extracted with DCM (2×) and the combined organic extracts were washed with brine and dried (Na2SO4). Evaporation of the solvent yielded the title compound as a white solid which was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6, 300K) δ 7.50 (1H, t, J=7.8 Hz), 7.18 (1H, d, J=7.3 Hz), 6.65 (1H, d, J=8.3 Hz), 6.28 (2H, bs), 3.79 (3H, s). MS (ES+) C7H8N2O2 requires: 152, found: 153 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 20 h
  3. temperatureAfter cooling down
  4. additionthe residue was added
  5. extractionThe aqueous phase was extracted with DCM (2×)
  6. washthe combined organic extracts were washed with brine
  7. dry with materialdried (Na2SO4)
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-c9f213f305c34184a090ea06e72de30e
Source dataset
uspto-grants-2013_01
Patent number
US08362030B2

Reaction notes

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