Potassium Hydroxide → HCID 178432821, compound

HRID 993294Notes

Reaction equation

HRID 993294 reaction equation
[OH-].[K+].[CH:3]([O:6][C:7]1[C:8]([CH3:17])=[N:9][CH:10]=[C:11]([CH:16]=1)[C:12]([O:14]C)=[S:13])([CH3:5])[CH3:4]>O.CO>[CH:3]([O:6][C:7]1[C:8]([CH3:17])=[N:9][CH:10]=[C:11]([CH:16]=1)[C:12]([OH:14])=[S:13])([CH3:5])[CH3:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 22145815HCID 22145815, compound

Product 1

HCID 178432821HCID 178432821, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Potassium hydroxide (770 mg) in water (8 mL) is added to a solution of methyl 5-isopropyloxy-6-methylthionicotinoate (1.1 g) in methanol (15 mL) and the mixture stirred at room temperature for 6 hours. After concentrating in vacuo the residue is dissolved in water and acidified to pH 1 with concentrated aqueous hydrochloric acid. The mixture is extracted with ethyl acetate, the extracts washed with water and dried (MgSO4). The solvent is removed in vacuo to give 5-isopropyloxy-6-methylthionicotinic acid as a white solid, m.p. 154-5° C.

Workup

  1. concentrationAfter concentrating in vacuo the residue
  2. dissolutionis dissolved in water
  3. extractionThe mixture is extracted with ethyl acetate
  4. washthe extracts washed with water
  5. dry with materialdried (MgSO4)
  6. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-5158631eb6934004b1b00a12f62e7f04
Source dataset
uspto-grants-2002_10
Patent number
US06472412B1

Reaction notes

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