Sulfuric Acid → 3-(Ethylsulfanyl)pyridine-2-carboxylic acid
Reaction equation
[CH2:1]([S:3][C:4]1[C:5]([C:10]#N)=[N:6][CH:7]=[CH:8][CH:9]=1)[CH3:2].S(=O)(=O)(O)[OH:13].[OH-:17].[Na+]>O>[CH2:1]([S:3][C:4]1[C:5]([C:10]([OH:13])=[O:17])=[N:6][CH:7]=[CH:8][CH:9]=1)[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
A mixture of 1.4 g of 3-ethylsulfanylpyridine-2-carbonitrile, 15 mL of concentrated sulfuric acid and 5 mL of water was stirred at 130° C. for 2 hours. Water was poured to the reaction mixture cooled to room temperature, sodium hydroxide was added thereto, and the mixture was extracted with ethyl acetate. Concentrated hydrochloric acid was added to the aqueous layer, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 1.15 g of 3-ethylsulfanylpicolinic acid.
Workup
- temperaturecooled to room temperature
- extractionthe mixture was extracted with ethyl acetate
- additionConcentrated hydrochloric acid was added to the aqueous layer
- extractionthe mixture was extracted with chloroform
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-a5e4d1157f8e4258847cbcba5b18752b
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09185910B2
Reaction notes
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