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

HRID 385542Notes

Reaction equation

HRID 385542 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[CH:15][C:16](=[O:26])[N:17]2[CH2:20][CH:21]2OCC[O:22]2)=[N:12][CH:11]=1)#[N:9].[OH-].[Na+]>>[C:8]([C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[CH:15][C:16](=[O:26])[N:17]2[CH2:20][CH:21]=[O:22])=[N:12][CH:11]=1)#[N:9]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 68927458HCID 68927458, compound

Product 1

HCID 86633192(7-cyano-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehydeYield 50.5%

Procedure

To 5 mL of 90% trifluoroacetic acid, 215 mg of 7-cyano-1-(1,3-dioxolan-2-ylmethyl)-1,5-naphthyridin-2(1H)-one was dissolved, and the resultant solution was stirred at 60° C. for 7 hours. After the reaction mixture was cooled to room temperature and alkalified with a 10% aqueous sodium hydroxide solution, the solvent was then distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using silica gel; Silica Gel 60 made by KANTO CHEMICAL CO., INC., and an eluent of ethyl acetate:hexane=1:1, and washed with water to obtain 90 mg of (7-cyano-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde as a light yellow solid.

Workup

  1. distillationthe solvent was then distilled off under reduced pressure
  2. customThe resultant residue was purified by silica gel column chromatography
  3. wash, and an eluent of ethyl acetate:hexane=1:1, and washed with water

Sources & evidence

ORD record
ord-2a6d80d8878947d483b19800d5951cab
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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