Potassium Hydroxide → HCID 22145751, compound

HRID 1994337Notes

Reaction equation

HRID 1994337 reaction equation
[OH-].[K+].[CH:3]1([O:8][C:9]2[C:10]([O:19][CH3:20])=[N:11][CH:12]=[C:13]([CH:18]=2)[C:14]([O:16]C)=[O:15])[CH2:7][CH2:6][CH2:5][CH2:4]1>O.CO>[CH:3]1([O:8][C:9]2[C:10]([O:19][CH3:20])=[N:11][CH:12]=[C:13]([CH:18]=2)[C:14]([OH:16])=[O:15])[CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 22145812Methyl 5-(cyclopentyloxy)-6-methoxy-3-pyridinecarboxylate

Product 1

HCID 22145751HCID 22145751, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of potassium hydroxide (168 mg) in water (1 mL) is added to a solution of methyl 5-cyclopentyloxy-6-methoxynicotinoate (250 mg) in methanol (3 mL) and the mixture stirred for 4 hours then allowed to stand at room temperature overnight. The mixture is concentrated, the residue dissolved in water and the mixture adjusted to pH 6 by the addition of concentrated hydrochloric acid. The mixture is extracted with ethyl acetate, the extracts dried (MgSO4) and concentrated to give a cream solid. The solid is dried at 100° C. to give 5-cyclopentyloxy-6-methoxynicotinic acid (140 mg), m.p. 191-2° C. [Elemental analysis: —C, 60.7; H, 6.43; N, 5.78%. calculated: —C, 60.75; H, 6.37; N, 5.90%.].

Workup

  1. waitto stand at room temperature overnight
  2. concentrationThe mixture is concentrated
  3. dissolutionthe residue dissolved in water
  4. additionthe mixture adjusted to pH 6 by the addition of concentrated hydrochloric acid
  5. extractionThe mixture is extracted with ethyl acetate
  6. dry with materialthe extracts dried (MgSO4)
  7. concentrationconcentrated
  8. customto give a cream solid
  9. customThe solid is dried at 100° C.

Sources & evidence

ORD record
ord-71d795abd67541e9a308124f2f791b9c
Source dataset
uspto-grants-2010_01
Patent number
US07652144B2

Reaction notes

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