Water → (3-Ethynyl-quinolin-6-yloxy)-metoxy-acetic acid

HRID 1962858Notes

Reaction equation

HRID 1962858 reaction equation
C[O:2][C:3](=[O:24])[CH:4]([O:22][CH3:23])[O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][C:10]([C:16]#[C:17][Si](C)(C)C)=[CH:9]2.[OH-].[Na+].C(OCC)(=O)C.O>C(O)C>[C:16]([C:10]1[CH:11]=[N:12][C:13]2[C:8]([CH:9]=1)=[CH:7][C:6]([O:5][CH:4]([O:22][CH3:23])[C:3]([OH:24])=[O:2])=[CH:15][CH:14]=2)#[CH:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 59565426Methoxy-(3-trimethylsilanylethynyl-quinolin-6-yloxy)-acetic acid methyl ester

Product 1

HCID 59565329(3-Ethynyl-quinolin-6-yloxy)-metoxy-acetic acidYield 77.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methoxy-(3-trimethylsilanylethynyl-quinolin-6-yloxy)-acetic acid methyl ester (1.99 g) in ethanol (14 mL) was added a solution of sodium hydroxide 2N (4 mL) at 0° C. The reaction mixture was stirred at room temperature for 1 hour. Ethyl acetate and water were added. The mixture was stirred. The two layers were separated. The aqueous layer was acidified at pH 1 with HCl 2N. Then it was extracted with ethyl acetate (twice). The organic layer was dried over sodium sulphate, filtered and concentrated under reduced pressure to give (3-ethynyl-quinolin-6-yloxy)-metoxy-acetic acid (1.15 g) as an orange solid.

Workup

  1. stirringThe mixture was stirred
  2. customThe two layers were separated
  3. extractionThen it was extracted with ethyl acetate (twice)
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-306f31706ec64ccca1802d314cdfb384
Source dataset
uspto-grants-2013_04
Patent number
US08415272B2

Reaction notes

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