Potassium Hydroxide → 5-Chloro-2-(3,5-dimethylphenyl)quinoline

HRID 2275971Notes

Reaction equation

HRID 2275971 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9]O.[CH3:11][C:12]1[CH:17]=[C:16]([C:18]([CH3:20])=O)[CH:15]=[C:14]([CH3:21])[CH:13]=1.[OH-].[K+]>C1(C)C=CC=CC=1>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]2[C:3]=1[CH:9]=[CH:20][C:18]([C:16]1[CH:17]=[C:12]([CH3:11])[CH:13]=[C:14]([CH3:21])[CH:15]=1)=[N:1]2

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 149211-(3,5-Dimethylphenyl)ethan-1-oneHCID 21925574(2-Amino-6-chlorophenyl)methanol

Product 1

HCID 681069905-Chloro-2-(3,5-dimethylphenyl)quinolineYield 32%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(2-Amino-6-chlorophenyl)methanol (16 g, 102 mmol), 3,5-dimethylacetophenone (22.6 g, 152 mmol), RuCl2(PPh3)3 (0.973 g, 1.015 mmol), and KOH (10.25 g, 183 mmol) were refluxed in 270 mL of toluene for 18 h. Water was collected from the reaction using a Dean-stark trap. The reaction mixture was allowed to cool to room temperature, filtered through a silica gel plug and eluted with 5% ethyl acetate in hexanes. The product was further purified by Kugelrohr distillation to give 23.5 g of crude product, which was crystallized from 60 mL of MeOH to give 8.6 g (32% yield) of the desired product.

Workup

  1. customWater was collected from the reaction
  2. filtrationfiltered through a silica gel plug
  3. washeluted with 5% ethyl acetate in hexanes
  4. distillationThe product was further purified by Kugelrohr distillation
  5. customto give 23.5 g of crude product, which
  6. customwas crystallized from 60 mL of MeOH

Sources & evidence

ORD record
ord-5ed37a77812647bb9131657e3508305a
Source dataset
uspto-grants-2015_09
Patent number
US09130177B2

Reaction notes

Loading…