Potassium Hydroxide → HCID 178432821, compound

HRID 1994345Notes

Reaction equation

HRID 1994345 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-b28dc53cae1a4d8cbc71a7226a27853f
Source dataset
uspto-grants-2010_01
Patent number
US07652144B2

Reaction notes

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