Ethyl 3-oxohexanoate → HCID 68518077, compound

HRID 1717335Notes

Reaction equation

HRID 1717335 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[NH:9][CH2:8][CH2:7]2)=[N+:2]=[N-:3].O=[C:16]([CH2:23][CH2:24][CH3:25])[CH2:17][C:18]([O:20]CC)=[O:19].[O-]CC.[Na+]>C(O)C>[O:14]=[C:10]1[C:11]2[C:6](=[CH:5][C:4]([N:1]3[C:16]([CH2:23][CH2:24][CH3:25])=[C:17]([C:18]([OH:20])=[O:19])[N:3]=[N:2]3)=[CH:13][CH:12]=2)[CH2:7][CH2:8][NH:9]1

Participants

5

Reactant 3

HCID 238498Ethyl 3-oxohexanoateHCID 2723922Sodium ethoxideHCID 86629806HCID 86629806, compound

Product 1

HCID 68518077HCID 68518077, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 6-azido-3,4-dihydroisoquinolin-1(2H)-one (0.24 g) obtained in Example 132b) and ethyl 3-keto-n-hexanoate (0.25 ml) in ethanol (7 ml) was added 28% sodium ethoxide in ethanol solution (0.60 ml) at room temperature, and the mixture was stirred for 3 hr. The solvent was evaporated under reduced pressure, and water was added to the obtained residue. The mixture was washed with ethyl acetate, 1N hydrochloric acid was added to acidify the aqueous solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound as a yellow solid (0.22 g, 57%).

Workup

  1. customThe solvent was evaporated under reduced pressure, and water
  2. additionwas added to the obtained residue
  3. washThe mixture was washed with ethyl acetate, 1N hydrochloric acid
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-72d9041d3be9446e9ba27aaedde1e8f1
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

Loading…