Lithium Chloride → HCID 22139714, compound

HRID 1825865Notes

Reaction equation

HRID 1825865 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:18]([O:19]C)=[CH:17][CH:16]=[C:15]3[C:10]=2[CH:11]=[CH:12][C:13]([S:21]([CH3:24])(=[O:23])=[O:22])=[N:14]3)=[CH:4][CH:3]=1.[Li+].[Cl-]>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[C:18]([OH:19])=[CH:17][CH:16]=[C:15]3[C:10]=2[CH:11]=[CH:12][C:13]([S:21]([CH3:24])(=[O:22])=[O:23])=[N:14]3)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 433294Lithium ChlorideHCID 22139687HCID 22139687, compound

Product 1

HCID 22139714HCID 22139714, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(4-Fluoro-phenylsulfanyl)-2-methanesulfonyl-6-methoxy-quinoline 102 (1 g) was dissolved in 5 mL DMF and treated with 500 mg LiCl and refluxed overnight. This mixture was partitioned between dilute HCl and EtOAc. The product was purified by chromatography (1:1 EtOAc/hexane) to provide 5-(4-fluoro-phenylsulfanyl)-2-methanesulfonyl-quinolin-6-ol; 401 (800 mg); ([M+H]+)=350.

Workup

  1. temperaturerefluxed overnight
  2. customThis mixture was partitioned between dilute HCl and EtOAc
  3. customThe product was purified by chromatography (1:1 EtOAc/hexane)

Sources & evidence

ORD record
ord-9bd4ea4631584e7f907b51e5a055c02f
Source dataset
uspto-grants-2006_05
Patent number
US07049325B2

Reaction notes

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