Sodium Hydroxide → HCID 58114928, compound

HRID 241771Notes

Reaction equation

HRID 241771 reaction equation
C([O:3][C:4](=[O:19])[CH:5]([C:11]1[C:16]([Cl:17])=[CH:15][C:14]([Cl:18])=[CH:13][N:12]=1)C(OCC)=O)C.[OH-].[Na+]>CO>[Cl:17][C:16]1[C:11]([CH2:5][C:4]([OH:19])=[O:3])=[N:12][CH:13]=[C:14]([Cl:18])[CH:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57950225HCID 57950225, compound

Product 1

HCID 58114928HCID 58114928, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(3,5-dichloro-pyrid-2-yl)-malonic acid diethyl ester (118.5 g) (prepared as described in WO 07/101,859) in methanol (1 ml) was added aqueous sodium hydroxide (47 g dissolved in 300 ml water). The reaction mixture was heated to 80° C. for 1 hour. The methanol was evaporated and the pH of the aqueous phase adjusted to pH 4 by addition of glacial acetic acid and then extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate and concentrated to give (3,5-dichloro-pyrid-2-yl)-acetic acid as an off-white solid (50 g). 1H-NMR (400 MHz, CDCl3): 4.04 (s, 2H), 7.81 (d, 1H), 8.45 (d, 1H) ppm.

Workup

  1. customThe methanol was evaporated
  2. additionthe pH of the aqueous phase adjusted to pH 4 by addition of glacial acetic acid
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-826d9b26b4fd4a5bb827cb7329fabd97
Source dataset
uspto-grants-2014_02
Patent number
US08653078B2

Reaction notes

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