Methyl p-toluenesulfonate → HCID 12596828, compound

HRID 2397923Notes

Reaction equation

HRID 2397923 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]=[CH:9]2)([O-:3])=[O:2].[C:14]1([CH3:25])[CH:19]=[CH:18][C:17]([S:20]([O:23]C)(=[O:22])=[O:21])=[CH:16][CH:15]=1>CN(C)C=O>[C:14]1([CH3:25])[CH:15]=[CH:16][C:17]([S:20]([O-:23])(=[O:21])=[O:22])=[CH:18][CH:19]=1.[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N+:8]([CH3:14])=[CH:9]2)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 690855-Nitroisoquinoline

Product 1

HCID 12596828HCID 12596828, compoundYield 169.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Nitroisoquinoline (25 g) and methyl p-toluenesulfonate (26.8 g) were dissolved in dimethylformamide (80 ml) and allowed to stand at room temperature for three days. If a crystalline cake had not formed at the end of this time, the solution was either seeded or scratched to initiate precipitation of the product. The supernatant was decanted and ethyl acetate was added to this until no more precipitation was evident. This precipitate was collected by filtration and combined with the first precipitate. The product was recrystallized from ethanol-ethyl acetate to yield 43.9 g of yellow crystals, m.p. 144°-144.7°C.

Workup

  1. customIf a crystalline cake had not formed at the end of this time
  2. customprecipitation of the product
  3. customThe supernatant was decanted
  4. additionethyl acetate was added to this
  5. customuntil no more precipitation
  6. filtrationThis precipitate was collected by filtration
  7. customThe product was recrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-9d3295f17de14987b2073812a1a0424b
Source dataset
uspto-grants-1977_05
Patent number
US04022900

Reaction notes

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