Potassium Hydroxide → HCID 178432820, compound

HRID 1994343Notes

Reaction equation

HRID 1994343 reaction equation
[OH-].[K+].[CH:3]1([O:8][C:9]2[C:10]([CH3:19])=[N:11][CH:12]=[C:13]([CH:18]=2)[C:14]([O:16]C)=[S:15])[CH2:7][CH2:6][CH2:5][CH2:4]1>O.CO>[CH:3]1([O:8][C:9]2[C:10]([CH3:19])=[N:11][CH:12]=[C:13]([CH:18]=2)[C:14]([OH:16])=[S:15])[CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 22145703HCID 22145703, compound

Product 1

HCID 178432820HCID 178432820, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of potassium hydroxide (582 mg) in water (6 mL) is added to a stirred solution of methyl 5-cyclopentyloxy-6-methylthionicotinoate (920 mg) in methanol at room temperature and the mixture stirred for 6 hours. After concentrating in vacuo the mixture is diluted with water and acidified to pH 1 with aqueous 2 M hydrochloric acid. The product is extracted into ethyl acetate, the extracts treated with decolourising charcoal, dried (MgSO4) and evaporated. The residue is triturated with n-pentane to give 5-cyclopentyloxy-6-methylthionicotinic acid (640 mg) as a white solid, m.p. 177-8° C. [Elemental analysis: —C, 56.90; H, 6.02; N, 5.52%. calculated: —C, 56.90; H, 5.97; N, 5.53%.].

Workup

  1. concentrationAfter concentrating in vacuo the mixture
  2. additionis diluted with water
  3. extractionThe product is extracted into ethyl acetate
  4. additionthe extracts treated with decolourising charcoal
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue is triturated with n-pentane

Sources & evidence

ORD record
ord-72cc7c943abc49a9a2fd50faf778e406
Source dataset
uspto-grants-2010_01
Patent number
US07652144B2

Reaction notes

Loading…