Potassium Hydroxide → HCID 22145851, compound

HRID 1092846Notes

Reaction equation

HRID 1092846 reaction equation
[OH-].[K+].[CH:3]1([O:8][C:9]2[C:14]([O:15][CH3:16])=[CH:13][N:12]=[C:11]([C:17]([O:19]C)=[O:18])[CH:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1>O.CO>[CH:3]1([O:8][C:9]2[C:14]([O:15][CH3:16])=[CH:13][N:12]=[C:11]([C:17]([OH:19])=[O:18])[CH:10]=2)[CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 22145895HCID 22145895, compound

Product 1

HCID 22145851HCID 22145851, compoundYield 36.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of potassium hydroxide (4.71 g) in water (32 mL) is added to a solution of methyl 4-cyclopentyloxy-5-methoxypyridine-2-carboxylate (7.03 g) in methanol (188 mL) and the mixture allowed to stand for 45 hours. After concentrating in vacuo the residue is dissolved in water, washed with ethyl acetate and basified to pH 5 with concentrated aqueous hydrochloric acid. The mixture is extracted with dichloromethane, the extracts dried (MgSO4) and evaporated to give 4-cyclopentyloxy-5-methoxypyridine-2-carboxylic acid (2.4 g) as a white solid.

Workup

  1. concentrationAfter concentrating in vacuo the residue
  2. dissolutionis dissolved in water
  3. washwashed with ethyl acetate and basified to pH 5 with concentrated aqueous hydrochloric acid
  4. extractionThe mixture is extracted with dichloromethane
  5. dry with materialthe extracts dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-decbfb763a664cbc8ec20bbf028674fe
Source dataset
uspto-grants-2012_03
Patent number
US08129537B2

Reaction notes

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