Ethyl bromoacetate → Ethyl [(isoquinolin-5-yl)oxy]acetate

HRID 2269639Notes

Reaction equation

HRID 2269639 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C1CCN2C(=NCCC2)CC1>C(#N)C>[CH:7]1[C:8]2[C:3](=[C:2]([O:1][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 30386Isoquinolin-5-olHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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. dissolutionthe resultant residue was redissolved in 1N-HCl
  3. washwashed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe dried solution was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5c1ccec77f9a462b9307eb4d6a65ca32
Source dataset
uspto-grants-2001_12
Patent number
US06329502B1

Reaction notes

Loading…