Phosphorus oxychloride → 1-(6-Bromo-4-chloroquinolin-3-yl)-2-methylpropan-1-one

HRID 2271514Notes

Reaction equation

HRID 2271514 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:16])[CH:13]([CH3:15])[CH3:14])=[C:5]2O.C(=O)(O)[O-].[Na+].C(OCC)(=O)C.P(Cl)(Cl)([Cl:31])=O>>[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:16])[CH:13]([CH3:15])[CH3:14])=[C:5]2[Cl:31]

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 86584982Sodium bicarbonate ethyl acetateHCID 178450272HCID 178450272, compound

Product 1

HCID 680919931-(6-Bromo-4-chloroquinolin-3-yl)-2-methylpropan-1-oneYield 89%

Conditions

Temperature
85 °C

Procedure

1-(6-Bromo-4-hydroxyquinolin-3-yl)-2-methylpropan-1-one (16.0 g, 54.4 mmol) was added to phosphoryl chloride (160 mL) and the reaction was stirred at 85° C. for 1.5 h. The reaction mixture was cooled and slowly poured into a 2:1 solution of satd. aq. sodium bicarbonate/ethyl acetate at 0° C. The organic layer was separated and was washed with satd. aq. sodium bicarbonate and brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford the desired product (14.8 g, 89%) as a yellow solid: ESI MS m/z 312 [C13H11BrClNO+H]+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. additionslowly poured into a 2:1 solution of satd
  3. customat 0° C
  4. customThe organic layer was separated
  5. washwas washed with satd
  6. dry with materialaq. sodium bicarbonate and brine, dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f569a67eaae148e2ab98e47ffeeb9d99
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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