Methanol → Methyl 5-aminopyridine-2-carboxylate

HRID 341503Notes

Reaction equation

HRID 341503 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.S(=O)(=O)(O)O.[CH3:16]O>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:16])=[O:9])=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 41797265-Aminopyridine-2-carboxylic acid

Product 1

HCID 12457877Methyl 5-aminopyridine-2-carboxylate

Procedure

5-Aminopyridine-2-carboxylic acid (1.60 g, 11.6 mmol) was dissolved in MeOH (100 mL) and concentrated sulfuric acid (1.7 mL, 12.8 mmol) was added and the mixture was heated to 80 C for 5 hours. The reaction mixture was concentrated under vacuum, neutralised by adding 1M aq. sodium bicarbonate and extracted with EtOAc. The organic layer was dried over sodium sulfate and concentrated under vacuum to afford the title compound as a pale yellow solid (1.813 g, quant.). Method B HPLC-MS: MH+ requires m/z=153 Found: m/z=153, Rt=0.35 min (by MS).

Workup

  1. temperaturethe mixture was heated to 80 C for 5 hours
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. additionby adding 1M aq. sodium bicarbonate
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d4b3a68ad0e94b58b6fd0e51745b9bbb
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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