Hydrochloric Acid → Methyl 5-aminopyridine-3-carboxylate

HRID 399801Notes

Reaction equation

HRID 399801 reaction equation
C(OC([NH:8][C:9]1[CH:10]=[C:11]([C:15]([O:17][CH3:18])=[O:16])[CH:12]=[N:13][CH:14]=1)=O)(C)(C)C.Cl.C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.O>[NH2:8][C:9]1[CH:10]=[C:11]([C:15]([O:17][CH3:18])=[O:16])[CH:12]=[N:13][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 18945232Methyl 5-(tert-butoxycarbonylamino)nicotinate

Product 1

HCID 1514432Methyl 5-aminopyridine-3-carboxylateYield 59%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of methyl 5-tert-butoxycarbonylamino-3-pyridinecarboxylate (5.7 g) and conc. hydrochloric acid (11.4 ml) in methanol (57 ml) was stirred for 1 hour at 40° C. After being cooled to room temperature, the reaction mixture was poured into a mixture of ethyl acetate (100 ml) and water (50 ml) under stirring, and adjusted to pH 9.0 with 10% potassium carbonate aqueous solution. The organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was recrystallized from diethyl ether-methanol to afford methyl 5-amino-3-pyridinecarboxylate (2.03 g).

Workup

  1. temperatureAfter being cooled to room temperature
  2. stirringunder stirring
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was recrystallized from diethyl ether-methanol

Sources & evidence

ORD record
ord-9bd0f208d6964ccab1cec09a84c2b1dd
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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