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

HRID 1091091Notes

Reaction equation

HRID 1091091 reaction equation
[F: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>ClC(Cl)C>[Cl:23][CH2:13][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[N:8]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 15675913HCID 15675913, compound

Product 1

HCID 112410072-(Chloromethyl)-6-fluoroquinolineYield 63%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
100 °C

Procedure

6-Fluoro-2-methylquinoline N-oxide (2.70 g, 15.25 mmol) was added to a stirring solution of p-toluenesulfonyl chloride (2.9 g, 15.21 mmol) in dichloroethane (100 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 purified by flash chromatography (15:1 hexane/ethyl acetate) to afford 1.59 g (63%) 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
  7. customThe crude solid was purified by flash chromatography (15:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-594b55aaa1164d53880d6e1351d45fbb
Source dataset
uspto-grants-1992_01
Patent number
US05084463

Reaction notes

Loading…