Sodium Hydroxide → HCID 58674396, compound

HRID 1994148Notes

Reaction equation

HRID 1994148 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:13]=[C:14]([CH2:18][CH2:19][C:20]([O:22]C)=[O:21])[CH:15]=[CH:16][CH:17]=2)[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:13]=[C:14]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH:15]=[CH:16][CH:17]=2)[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58674419HCID 58674419, compound

Product 1

HCID 58674396HCID 58674396, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-(3-{[2-(acetylamino)pyridin-4-yl]oxy}phenyl)propanoate (184 mg, 0.59 mmol) in MeOH (5 mL) was added 1N NaOH solution (702 μL, 0.70 mmol). The reaction was stirred for 18 h. The solvents were evaporated and the residue was dissolved in water and acidified to pH=1 by addition of 1N HCl solution. The precipitate was filtered off and washed with water then hexane and dried under vacuum to yield the title compound as a white solid (112 mg, 63.7%). LCMS: (FA) ES+ 301.2 (M+1), ES− 299.3 (M−1).

Workup

  1. customThe solvents were evaporated
  2. dissolutionthe residue was dissolved in water
  3. additionacidified to pH=1 by addition of 1N HCl solution
  4. filtrationThe precipitate was filtered off
  5. washwashed with water
  6. dry with materialhexane and dried under vacuum

Sources & evidence

ORD record
ord-101aed757e454a54b6a6a31fcb63dc01
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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