Potassium Hydroxide → HCID 22145742, compound

HRID 1092837Notes

Reaction equation

HRID 1092837 reaction equation
[OH-].[K+].[CH:3]1([O:8][C:9]2[N:14]=[C:13]([C:15]([O:17]C3CCCC3)=[O:16])[CH:12]=[CH:11][C:10]=2[O:23][CH3:24])[CH2:7][CH2:6][CH2:5][CH2:4]1>O.CO>[CH:3]1([O:8][C:9]2[N:14]=[C:13]([C:15]([OH:17])=[O:16])[CH:12]=[CH:11][C:10]=2[O:23][CH3:24])[CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 22145790HCID 22145790, compound

Product 1

HCID 22145742HCID 22145742, compoundYield 49.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Potassium hydroxide (1.98 g) in water (12 mL) is added to a solution of cyclopentyl 6-cyclopentyloxy-5-methoxypyridine-2-carboxylate (3.6 g) in methanol (35 mL) and the mixture stirred at room temperature for 2.5 hours. The solution is concentrated to half of the original volume and diluted with water. The solution is acidified to pH 4 with concentrated hydrochloric acid and the product extracted with ethyl acetate. The extracts are dried (MgSO4) and concentrated to give 6-cyclopentyloxy-5-methoxypyridine-2-carboxylic acid (1.38 g) as a yellow solid, m.p. 96-99° C.

Workup

  1. concentrationThe solution is concentrated to half of the original volume
  2. additiondiluted with water
  3. extractionthe product extracted with ethyl acetate
  4. dry with materialThe extracts are dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e9603be686894981964b33667b03925e
Source dataset
uspto-grants-2012_03
Patent number
US08129537B2

Reaction notes

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