Sodium Hydroxide → 2-(Isoquinolin-5-yloxy)acetic acid

HRID 2269640Notes

Reaction equation

HRID 2269640 reaction equation
[CH:1]1[C:10]2[C:5](=[C:6]([O:11][CH2:12][C:13]([O:15]CC)=[O:14])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[OH-].[Na+]>C(O)C>[CH:1]1[C:10]2[C:5](=[C:6]([O:11][CH2:12][C:13]([OH:15])=[O:14])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12902789Ethyl [(isoquinolin-5-yl)oxy]acetate

Product 1

HCID 129027902-(Isoquinolin-5-yloxy)acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 10 ml of acetonitrile, 1.0 g of 5-hydroxyisoquinoline and 1.52 ml of ethyl bromoacetate were added in the presence of 2.07 ml of DBU and the resultant mixture was refluxed for 8 hr. The reaction mixture was evaporated under reduced pressure and the resultant residue was redissolved in 1N-HCl, washed with ethyl acetate. The aqueous layer was made alkaline with sodium hydrogencarbonate and extracted with ethyl acetate. The extract was washed with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The dried solution was evaporated under reduced pressure and subjected to a silica gel column chromatography (chloroform) to give 1.46 g of ethyl 5-isoquinolyl-oxyacetate. The ester was dissolved in 30 ml of ethanol, mixed with 6.5 ml of 1N-NaOH aqueous solution and stirred for 12 hr. The reaction mixture was evaporated under reduced pressure, neutralized by the addition of 1N-HCl and the precipitated crystals were filtered, washed with water and dried to give 0.68 g of the title compound.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. additionneutralized by the addition of 1N-HCl
  3. filtrationthe precipitated crystals were filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-2dec656da98740548b7562a20ab92e48
Source dataset
uspto-grants-2001_12
Patent number
US06329502B1

Reaction notes

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