Hydrogen Bromide → HCID 22380865, compound

HRID 542256Notes

Reaction equation

HRID 542256 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[BrH:11]>>[Br-:11].[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][NH+:2]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 8405Isoquinoline

Product 1

HCID 22380865HCID 22380865, compoundYield 88.5%

Procedure

600 g of crude isoquinoline (purity 95% and total sulfur content 0.3%) and 759.6 g of 47% hydrobromic acid were stirred and cooled to undergo reaction. After the reaction, the resultant reactin mixture was distilled to expel water and then washed twice with acetone to afford 864.1 g of isoquinolinium bromide. By recrystallizing this isoquinolinium bromide from 6,881 g of isopropanol, 471.9 g (recovery ratio 85.9%) of refined isoquinolinium bromide having a total sulfur content of 22 ppm was obtained. The refined isoquinolinium bromide was recrystallized again from 6,498 g of isopropanol. The recrystallized isoquinolinium bromide (676.6 g) was dissolved in the same volume of water and decomposed with an aqueous 20% NaOH solution. Then, 495.3 g of the resultant liberated desulfurized isoquinoline was distilled, to afford 374.73 g (recovery ratio 62.5%) of refined isoquinoline (purity 99.7% and total sulfur content less than 1 ppm) was obtained.

Workup

  1. temperaturecooled
  2. customreaction
  3. customAfter the reaction
  4. distillationthe resultant reactin mixture was distilled
  5. washwashed twice with acetone

Sources & evidence

ORD record
ord-2c6a75c76f3a41bba9fe60de86b76c33
Source dataset
uspto-grants-1987_04
Patent number
US04656279

Reaction notes

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