Ammonium Hydroxide → 6-Bromo-2-chloro-4,8-dimethylquinoline

HRID 1850028Notes

Reaction equation

HRID 1850028 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[NH:8][C:7](=O)[CH:6]=[C:5]2[CH3:14].[NH4+].[OH-].O=P(Cl)(Cl)[Cl:19]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]=[C:7]([Cl:19])[CH:6]=[C:5]2[CH3:14]

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 145703026-Bromo-4,8-dimethylquinolin-2(1H)-one

Product 1

HCID 145703046-Bromo-2-chloro-4,8-dimethylquinolineYield 93%

Procedure

This quinolone (410 mg, 1.6 mmol) in POCl3 (5 mL) was refluxed for 2 h, then poured onto ice. The solution was neutralized to pH 7 by addition of NH4OH, and the resulting solid collected by filtration. Washing with water and drying in vacuo gave 6-bromo-2-chloro-4,8-dimethyl-quinoline (407 mg, 93%).

Workup

  1. additionpoured onto ice
  2. filtrationthe resulting solid collected by filtration
  3. washWashing with water
  4. customdrying in vacuo

Sources & evidence

ORD record
ord-34920d0619e94c57bd4c4fb0199b612d
Source dataset
uspto-grants-2015_02
Patent number
US08957049B2

Reaction notes

Loading…