Sulfuric Acid → 1-Isoquinolinyloxyacetaldehyde

HRID 495426Notes

Reaction equation

HRID 495426 reaction equation
C[O:2][C:3](OC)([O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][N:7]=1)[CH3:4].O1CCOCC1.S(=O)(=O)(O)O>O>[C:6]1([O:5][C:3](=[O:2])[CH3:4])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 312751,4-DioxaneHCID 693569501-Isoquinolinyloxyacetaldehyde dimethyl acetal

Product 1

HCID 178810501-IsoquinolinyloxyacetaldehydeYield 57.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 1-isoquinolinyloxyacetaldehyde dimethyl acetal (0.93 g, 4 mmol), dioxane (10 mL), water (15 mL) and conc. sulfuric acid (2 mmol) was heated at 85° C. for 2 h, then was quenched with saturated aqueous sodium hydrogen carbonate (100 mL). The resulting mixture was extracted with dichloromethane (2×100 mL) and the combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate (50 mL), dried over sodium sulfate and evaporated in vacuo to give the title compound (0.43 g, 57%).

Workup

  1. customwas quenched with saturated aqueous sodium hydrogen carbonate (100 mL)
  2. extractionThe resulting mixture was extracted with dichloromethane (2×100 mL)
  3. washthe combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate (50 mL)
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-c65813df7712480da7f56b4b9f71f2eb
Source dataset
uspto-grants-2005_09
Patent number
US06939871B2

Reaction notes

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