Sodium Hydroxide → 5-Cyclopropyl-6-(2-methoxyethoxy)-pyridine-2-carboxylic acid

HRID 927570Notes

Reaction equation

HRID 927570 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:13][CH2:12]2)=[C:7]([O:14][CH2:15][CH2:16][O:17][CH3:18])[N:6]=1)=[O:4].[OH-].[Na+]>C(O)C>[CH:11]1([C:8]2[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][C:7]=2[O:14][CH2:15][CH2:16][O:17][CH3:18])[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 710874485-Cyclopropyl-6-(2-methoxyethoxy)-pyridine-2-carboxylic acid methyl ester

Product 1

HCID 710874735-Cyclopropyl-6-(2-methoxyethoxy)-pyridine-2-carboxylic acidYield 83.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-cyclopropyl-6-(2-methoxyethoxy)-pyridine-2-carboxylic acid methyl ester (0.16 g, 0.6 mmol) and sodium hydroxide (31 mg, 0.7 mmol) in ethanol (40 mL) was heated to 90° C. for 2 h. The reaction mixture was evaporated, dissolved in water and extracted with ethyl acetate (30 mL). The pH of the aqueous layer was adjusted to 2 by addition of 1 N hydrochloric acid, the resulting precipitate was collected by filtration and dried in vacuo to give the title compound (0.11 g, 0.5 mmol; 73%) as yellow oil; MS: m/e=238.1 [M+H]+.

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutiondissolved in water
  3. extractionextracted with ethyl acetate (30 mL)
  4. additionThe pH of the aqueous layer was adjusted to 2 by addition of 1 N hydrochloric acid
  5. filtrationthe resulting precipitate was collected by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-f5d53a5971024a0ea5312aa6afe80453
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

Loading…