Potassium Hydroxide → 6-Bromo-7-chloro-2-(3,5-dimethylphenyl)quinoline

HRID 1505743

Reaction equation

HRID 1505743 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Br:9])=[CH:4][C:3]=1[CH2:10]O.[CH3:12][C:13]1[CH:18]=[C:17]([C:19]([CH3:21])=O)[CH:16]=[C:15]([CH3:22])[CH:14]=1.[OH-].[K+]>C1(C)C=CC=CC=1>[Br:9][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][C:6]=1[Cl:8])[N:1]=[C:19]([C:17]1[CH:18]=[C:13]([CH3:12])[CH:14]=[C:15]([CH3:22])[CH:16]=1)[CH:21]=[CH:10]2

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 149211-(3,5-Dimethylphenyl)ethan-1-oneHCID 67081018(2-Amino-5-bromo-4-chlorophenyl)methanol

Product 1

HCID 866849816-Bromo-7-chloro-2-(3,5-dimethylphenyl)quinolineYield 43.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(2-amino-5-bromo-4-chlorophenyl)methanol (8.2 g, 34.7 mmol), 3,5-dimethylacetophenone (8.22 g, 55.5 mmol), RuCl2(PPh3)3 (0.15 g, 0.173 mmol), and KOH (1.31 g, 23.4 mmol) was refluxed in 90 mL of toluene for 18 hours. Water was collected from the reaction using a Dean-Stark trap. The reaction mixture was allowed to cool to room temperature and filtered through a silica gel plug and eluted with DCM and purified by column chromatography, eluting with 2:1 (v/v) hexanes:DCM, to give 6-bromo-7-chloro-2-(3,5-dimethylphenyl)quinoline (5.2 g, 43.3%).

Workup

  1. customWater was collected from the reaction
  2. filtrationfiltered through a silica gel plug
  3. washeluted with DCM
  4. custompurified by column chromatography
  5. washeluting with 2:1 (v/v) hexanes

Sources & evidence

ORD record
ord-5b3c372cda554e3b92366ec5f333ff36
Source dataset
uspto-grants-2015_12
Patent number
US09217004B2

Linked notes

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