Sodium Hydroxide → 4-Bromo-7-chloro-3-(4-chloro-benzenesulfonyl)-quinoline

HRID 561045Notes

Reaction equation

HRID 561045 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](O)=[C:7]([S:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.O(Br)[Br:24].[P+5].[OH-].[Na+]>C(Cl)(Cl)Cl.C(N(CC)CC)C.O>[Br:24][C:6]1[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=[CH:8][C:7]=1[S:12]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 178419731HCID 178419731, compoundHCID 178527342HCID 178527342, compound

Product 1

HCID 670001544-Bromo-7-chloro-3-(4-chloro-benzenesulfonyl)-quinolineYield 77%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 7-chloro-3-(4-chloro-benzenesulfonyl)-quinolin-4-ol (0.5 g, 1.41 mmol) and phosphorus(V) oxybromide (1.2 g, 4.2 mmol) in chloroform (30 ml) and triethylamine (1 ml) was refluxed for 6 hours. The reaction mixture was diluted with water (30 ml) and the pH was adjusted to 10 with aqueous sodium hydroxide solution. The organic layer was separated, dried over sodium sulfate, filtered, and concentrated in vacuo. The obtained crude product was purified by crystallization from diethyl ether to obtain 0.45 g of the title compound in 77% yield.

Workup

  1. temperaturewas refluxed for 6 hours
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe obtained crude product
  7. customwas purified by crystallization from diethyl ether

Sources & evidence

ORD record
ord-04010ee87e9b40d597c275db2c18b120
Source dataset
uspto-grants-2011_11
Patent number
US08063220B2

Reaction notes

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