Water → 5-Methyl-6-sulfo-pyridine-2-carboxylic acid

HRID 927384

Reaction equation

HRID 927384 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH3:11].[S:12]([O-:15])([O-:14])=[O:13].[Na+].[Na+].O>C(O)C>[CH3:11][C:3]1[CH:4]=[CH:5][C:6]([C:8]([OH:10])=[O:9])=[N:7][C:2]=1[S:12]([OH:15])(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 24437Sodium SulfiteHCID 183244376-Chloro-5-methylpyridine-2-carboxylic acid

Product 1

HCID 866747445-Methyl-6-sulfo-pyridine-2-carboxylic acidYield 111.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
180 °C

Procedure

6-chloro-5-methyl-pyridine-2-carboxylic acid (0.85 g, 4.97 mmol) and sodium sulfite (CAN 7757-83-7, 1.5 g, 11.9 mmol) were added to water (3 mL) and ethanol (3 mL). The mixture was heated to 180° C. for 4 h in a sealed tube. After that the mixture was cooled to room temperature and a solid precipitated that was removed by filtration. The filtrate was concentrated and added to water (20 mL). The aqueous phase was washed with ethyl acetate (2×20 mL). Subsequently the aqueous phase was adjusted to pH=2 with 2 N hydrochloric acid. Water was removed in vacuo to give the product as solid (1.2 g); MS (EI): m/e=218.0 [M+H]+.

Workup

  1. temperatureAfter that the mixture was cooled to room temperature
  2. customa solid precipitated that
  3. customwas removed by filtration
  4. concentrationThe filtrate was concentrated
  5. additionadded to water (20 mL)
  6. washThe aqueous phase was washed with ethyl acetate (2×20 mL)
  7. customWater was removed in vacuo

Sources & evidence

ORD record
ord-0b6f6c8d7d5649ebbeb7d26be70d7d95
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Linked notes

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