Ethylene Glycol → 3-(1,3-Dioxolan-2-yl)isoquinoline

HRID 1780929Notes

Reaction equation

HRID 1780929 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH:11]=[O:12])[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:3]1[N:2]=[CH:1][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 231555Isoquinoline-3-carboxaldehyde

Product 1

HCID 190474993-(1,3-Dioxolan-2-yl)isoquinolineYield 89.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-isoquinolinecarboxaldehyde (7 g, 44.5 mmol), 5.5 g (88 mmol) of ethylene glycol, 400 ml of toluene and 1.1 g (4.4 mmol) of p-toluenesulfonic acid was refluxed for 16 h while separating the water formed. The mixture was cooled to room temperature and washed with sodium bicarbonate solution, water, and brine. The organic layer was dried over sodium sulfate, and concentrated in vacuo to afford 8 g (89.9%) of 3-(1,3-dioxolan-2-yl)isoquinoline (Formula XII: R2 =R7 =H).

Workup

  1. temperaturewas refluxed for 16 h
  2. customwhile separating the water
  3. customformed
  4. washwashed with sodium bicarbonate solution, water, and brine
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ba96baec63e2477e9126cc3d3a5c07f5
Source dataset
uspto-grants-1997_05
Patent number
US05631264

Reaction notes

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