4-Toluenesulfonyl chloride → 2-(Chloromethyl)-6-nitroquinoline

HRID 1091087Notes

Reaction equation

HRID 1091087 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=2)[N+:3]=1[O-].C1(C)C=CC(S([Cl:25])(=O)=O)=CC=1.C(OCC)(=O)C>ClC(Cl)C>[Cl:25][CH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 126651432-Methyl-6-nitroquinoline N-oxide

Product 1

HCID 126651392-(Chloromethyl)-6-nitroquinolineYield 56%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
100 °C

Procedure

2-Methyl-6-nitroquinoline N-oxide (13.0 g, 63.72 mmol) was added to a stirring solution of p-toluenesulfonyl chloride (13.5 g, 70.81 mmol) in dichloroethane (200 mL). The reaction was stirred overnight at 100° C. and then stirred at room temperature for 2 days. To the reaction mixture was added ethyl acetate. A solid precipitated and was filtered and recrystallized from acetone/water to afford 7.91 g (56%) of pure product.

Workup

  1. stirringstirred at room temperature for 2 days
  2. customA solid precipitated
  3. filtrationwas filtered
  4. customrecrystallized from acetone/water

Sources & evidence

ORD record
ord-a1dab87770854fa9a9af923665fddca7
Source dataset
uspto-grants-1992_01
Patent number
US05084463

Reaction notes

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