Sodium Carbonate → HCID 68091885, compound

HRID 2271530Notes

Reaction equation

HRID 2271530 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])[CH2:13][CH2:14][CH3:15])=[C:5]2O.P(Cl)(Cl)([Cl:20])=O.C(=O)([O-])[O-].[Na+].[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:16])[CH2:13][CH2:14][CH3:15])=[C:5]2[Cl:20]

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 178450273HCID 178450273, compound

Product 1

HCID 68091885HCID 68091885, compoundYield 98%

Conditions

Temperature
75 °C

Procedure

1-(6-bromo-4-hydroxyquinolin-3-yl)butan-1-one (3.73 g, 12.7 mmol) was added to phosphoryl chloride (37 mL) and the reaction was stirred at 75° C. for 2 h. After this time the reaction mixture was cooled to room temperature and slowly poured into a solution of satd. aq. sodium carbonate that was cooled to 0° C. The resultant mixture was extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by column chromatography (silica, ethyl acetate) afforded the desired product (3.90 g, 98%) as an off-white solid. ESI MS m/z 312 [C13H13BrClNO+H]+

Workup

  1. temperatureAfter this time the reaction mixture was cooled to room temperature
  2. additionslowly poured into a solution of satd
  3. extractionThe resultant mixture was extracted with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography (silica, ethyl acetate)

Sources & evidence

ORD record
ord-d210e2ed8e72439ca0064a6864399084
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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