Phosphorus oxychloride → 1-(6-Bromo-4-chloroquinolin-3-yl)propan-1-one

HRID 2271527Notes

Reaction equation

HRID 2271527 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](=[O:15])[CH2:13][CH3:14])=[C:5]2O.P(Cl)(Cl)([Cl:19])=O.C(=O)(O)[O-].[Na+]>[OH-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](=[O:15])[CH2:13][CH3:14])=[C:5]2[Cl:19]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178458757HCID 178458757, compound

Product 1

HCID 866928451-(6-Bromo-4-chloroquinolin-3-yl)propan-1-oneYield 96%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

1-(6-Bromo-4-hydroxyquinolin-3-yl)propan-1-one (21 g, 67.7 mmol) was added to phosphoryl chloride (80 mL). The resultant suspension was then heated to 85° C. and stirred for 1.5 h. The reaction mixture was cooled to room temperature and poured carefully into a mixture of saturated sodium bicarbonate (250 mL) and 2N aqueous sodium hydroxide (250 mL). The solution was then extracted with ethyl acetate, the combined organics were washed with water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the desired product (16 g, 96%) as a tan solid: APCI MS m/z 298 [C12H9BrClNO+H]+.

Workup

  1. extractionThe solution was then extracted with ethyl acetate
  2. washthe combined organics were washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b9155682872748e4b20ffa148397aaeb
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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