4-Toluenesulfonyl chloride → 6-Chloro-2-(chloromethyl)quinoline

HRID 1091092Notes

Reaction equation

HRID 1091092 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N+:8]([O-])=[C:7]([CH3:13])[CH:6]=[CH:5]2.C1(C)C=CC(S([Cl:23])(=O)=O)=CC=1.CCCCCC.C(OCC)(=O)C>ClC(Cl)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:13][Cl:23])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 156759166-Chloro-2-methyl-1-oxo-1lambda~5~-quinolineHCID 21226206Ethyl acetate hexane

Product 1

HCID 125598416-Chloro-2-(chloromethyl)quinolineYield 54.1%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
100 °C

Procedure

6-Chloro-2-methylquinoline N-oxide (1.73 g, 8.1 mmol) was added to a stirring solution of p-toluenesulfonyl chloride (1.7 g, 8.96 mmol) in dichloroethane (80 mL). The reaction mixture was heated to 100° C. overnight under N2, cooled and concentrated, partitioned between 10% K2CO3 /ethyl acetate, dried over MgSO4, and evaporated under reduced pressure to afford a solid. The crude solid was purifed by flash chromatography (4:1 hexane/ethyl acetate) to afford 0.93 g (52%) of pure product as an off white solid.

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. custompartitioned between 10% K2CO3 /ethyl acetate
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure
  6. customto afford a solid

Sources & evidence

ORD record
ord-6a654d0bf65a47ea935667e45b34b065
Source dataset
uspto-grants-1992_01
Patent number
US05084463

Reaction notes

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