Potassium Hydroxide → HCID 22145742, compound

HRID 1994340Notes

Reaction equation

HRID 1994340 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-a1a0bf17827e497b8dba6249fd4142f6
Source dataset
uspto-grants-2010_01
Patent number
US07652144B2

Reaction notes

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