Potassium Hydroxide → 5-(((4-Methoxybenzyl)-oxy)methyl)furo[2,3-b]pyridine-2-carboxylic acid

HRID 931387Notes

Reaction equation

HRID 931387 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][O:8][CH2:9][C:10]2[CH:11]=[C:12]3[CH:18]=[C:17]([C:19](N(C)C)=[O:20])[O:16][C:13]3=[N:14][CH:15]=2)=[CH:5][CH:4]=1.[OH-:26].[K+]>CO.O>[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][O:8][CH2:9][C:10]2[CH:11]=[C:12]3[CH:18]=[C:17]([C:19]([OH:26])=[O:20])[O:16][C:13]3=[N:14][CH:15]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 900505425-(((4-Methoxybenzyl)-oxy)-methyl)-N,N-dimethylfuro[2,3-b]pyridine-2-carboxamide

Product 1

HCID 900505445-(((4-Methoxybenzyl)-oxy)methyl)furo[2,3-b]pyridine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In a sealed tube, a mixture of a solution of 5-(((4-methoxybenzyl)-oxy)-methyl)-N,N-dimethylfuro[2,3-b]pyridine-2-carboxamide (2.4 g, 7.1 mmol) in methanol (28 mL) and a solution of potassium hydroxide (0.79 g, 14 mmol) in water (7 mL) was heated at reflux for 1 h. After cooling to ambient temperature, the reaction mixture was partitioned between saturated aqueous citric acid solution and ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated to give the title compound. MS: m/z=314.2 (M+1).

Workup

  1. temperatureat reflux for 1 h
  2. customthe reaction mixture was partitioned between saturated aqueous citric acid solution and ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fc5c552267f14a2384864584ef4e423a
Source dataset
uspto-grants-2016_03
Patent number
US09296750B2

Reaction notes

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