Ethylene Glycol → HCID 19047578, compound

HRID 1780919Notes

Reaction equation

HRID 1780919 reaction equation
[C:1]1([CH:11]=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[CH2:13](O)[CH2:14][OH:15].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:12]1[CH2:13][CH2:14][O:15][CH:11]1[C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 265306Isoquinoline-1-carbaldehyde

Product 1

HCID 19047578HCID 19047578, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-isoquinolinecarboxaldehyde (7.2 g, 46 mmol), 5.7 g (92 mmol) of ethylene glycol, 200 ml of toluene and 2.3 g (12 mmol) of p-toluenesulfonic acid under argon in a 3 neck-flask equipped with a Dean-Stark Trap was refluxed for 6 h separating the water. The mixture was cooled to room temperature, and poured into an ice-cold 10% sodium carbonate solution. The aqueous layer was extracted with ether, the combined organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo to afford 9.3 g of 1-(1,3-dioxolan-2-yl)isoquinoline.

Workup

  1. customequipped with a Dean-Stark Trap
  2. temperaturewas refluxed for 6 h
  3. customseparating the water
  4. additionpoured into an ice-cold 10% sodium carbonate solution
  5. extractionThe aqueous layer was extracted with ether
  6. washthe combined organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e72d322566874e22b4fe3d4c4cb4dd39
Source dataset
uspto-grants-1997_05
Patent number
US05631264

Reaction notes

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