Trifluoroacetic acid → (7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde

HRID 385535Notes

Reaction equation

HRID 385535 reaction equation
FC(F)(F)C(O)=O.[O:8]1CCO[CH:9]1[CH2:13][N:14]1[C:23]2[C:18](=[N:19][CH:20]=[C:21]([O:24][CH3:25])[CH:22]=2)[CH:17]=[CH:16][C:15]1=[O:26].[OH-].[Na+]>C(Cl)(Cl)Cl>[CH3:25][O:24][C:21]1[CH:22]=[C:23]2[C:18]([CH:17]=[CH:16][C:15](=[O:26])[N:14]2[CH2:13][CH:9]=[O:8])=[N:19][CH:20]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 578152071-(1,3-dioxolan-2-ylmethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one

Product 1

HCID 57815194(7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 184 mL of 80% trifluoroacetic acid, 4.60 g of 1-(1,3-dioxolan-2-ylmethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one was dissolved, and the resultant solution was stirred at room temperature for 11 hours and at 60° C. for 3.5 hours. The reaction mixture was charged with chloroform and alkalified with a 10% aqueous sodium hydroxide solution under cooling with ice. The organic layer was separated, and washed with an aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain (7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde as a yellow solid.

Workup

  1. temperatureunder cooling with ice
  2. customThe organic layer was separated
  3. washwashed with an aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-dfd2f72356074fdd9d8fe6e947f8561e
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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