Water → 5-(4-Nitrophenylsulfanyl)isoquinoline

HRID 619712Notes

Reaction equation

HRID 619712 reaction equation
[C:1]([S:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[CH:12]=[CH:13][N:14]=[CH:15]2)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4]C=1.C[O-].[Na+].[N+:23](C1C=CC(F)=CC=1)([O-:25])=[O:24].O>CO.C(Cl)(Cl)Cl>[N+:23]([C:6]1[CH:7]=[CH:2][C:1]([S:9][C:10]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:11]=2[CH:12]=[CH:13][N:14]=[CH:15]3)=[CH:4][CH:5]=1)([O-:25])=[O:24]

Participants

7

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 10942334Sodium MethoxideHCID 21846970HCID 21846970, compound

Product 1

HCID 154356845-(4-Nitrophenylsulfanyl)isoquinolineYield 90.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

5-Benzoylsulfanylisoquinoline 1.41 g (5.3 mmol) was dissolved in a mixture solution of methanol (50 ml) and chloroform (5 ml), sodium methoxide 500 mg (9.3 mmol) was added, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, the resulting residue was dissolved in DMF 50 ml, 4-nitrofluorobenzene 0.75 g (5.3 mmol) was added, and the mixture was heated and stirred at 100° C. for 3.5 hours. After cooling, water was added to the reaction mixture, the resulting precipitate was collected and washed with water to obtain 5-(4-nitrophenylsulfanyl)isoquinoline 1.36 g (90.9%).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe resulting residue was dissolved in DMF 50 ml
  4. temperaturethe mixture was heated
  5. stirringstirred at 100° C. for 3.5 hours
  6. temperatureAfter cooling
  7. customthe resulting precipitate was collected
  8. washwashed with water

Sources & evidence

ORD record
ord-dcef253b72424f208439b7b15c8f5ca5
Source dataset
uspto-grants-1999_09
Patent number
US05959107

Reaction notes

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