Sodium Bicarbonate → HCID 59398341, compound

HRID 39903Notes

Reaction equation

HRID 39903 reaction equation
[O:1]1CCO[CH:2]1[CH2:6][N:7]1[C:16]2[C:11](=[CH:12][C:13]([Br:17])=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]1=[O:18].C(=O)([O-])O.[Na+]>FC(F)(F)C(O)=O>[Br:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:7]([CH2:6][CH:2]=[O:1])[C:8](=[O:18])[CH:9]=[CH:10]2

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 59398115HCID 59398115, compound

Product 1

HCID 59398341HCID 59398341, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
40 °C

Procedure

0.56 g of 1-(1,3-dioxolan-2-ylmethyl)-6-bromoquinolin-2(1H)-one was dissolved in 4.5 mL of 67% aqueous trifluoroacetic acid solution, and stirred at room temperature for 18.5 hours, at 40° C. for 7.5 hours, further at room temperature for 15 hours. After the reaction mixture was alkalized by adding aqueous saturated sodium hydrogen carbonate solution, it was extracted with ethyl acetate. The organic layer was washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give (6-bromo-2-oxoquinolin-1(2H)-yl)acetaldehyde as a pale yellow solid.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with aqueous saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-13a2fe39b296407baaf9335e4c4c88bc
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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