Hydrochloric Acid → 2-Isopropylsulfanyl-5-methyl-nicotinic acid

HRID 62875Notes

Reaction equation

HRID 62875 reaction equation
[CH:1]([S:4][C:5]1[C:10]([C:11]#N)=[CH:9][C:8]([CH3:13])=[CH:7][N:6]=1)([CH3:3])[CH3:2].[OH-:14].[K+].Cl.[OH2:17]>CS(C)=O>[CH:1]([S:4][C:5]1[N:6]=[CH:7][C:8]([CH3:13])=[CH:9][C:10]=1[C:11]([OH:17])=[O:14])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 901181222-Isopropylsulfanyl-5-methyl-pyridine-3-carbonitrile

Product 1

HCID 901181832-Isopropylsulfanyl-5-methyl-nicotinic acidYield 73%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

After 2-isopropylsulfanyl-5-methyl-pyridine-3-carbonitrile (0.186 g, 0.97 mmol) obtained in Step A was dissolved in water (0.4 mL) and DMSO (0.04 mL), KOH (0.76 g) was added thereto, and the mixture was stirred at 100° C. for 16 hours. After the termination of the reaction, 6N HCl aqueous solution was added thereto to adjust the pH of the reactant to 2, and the mixture was extracted with EtOAc. The organic layer was separated, dried with MgSO4, and concentrated under reduced pressure to obtain the title compound (0.15 g, 73%).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3b6193eb6f9940cfa0ee8459627dd774
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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