Water → 2-Ethoxy-6-formyl-5-nitronicotinonitrile

HRID 2407837Notes

Reaction equation

HRID 2407837 reaction equation
CN(C)C=[CH:4][C:5]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:8]([C:9]#[N:10])=[C:7]([O:16][CH2:17][CH3:18])[N:6]=1.O.I([O-])(=O)(=O)=[O:22].[Na+]>O1CCCC1>[CH2:17]([O:16][C:7]1[N:6]=[C:5]([CH:4]=[O:22])[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:8]=1[C:9]#[N:10])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 768067286-(2-(Dimethylamino)vinyl)-2-ethoxy-5-nitronicotinonitrile

Product 1

HCID 585040872-Ethoxy-6-formyl-5-nitronicotinonitrileYield 67.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the compound prepared in Example 445 (1.07 g) in tetrahydrofuran (20 mL) at ambient temperature was added water (20 mL), and to the resulting mixture was added sodium periodate (2.62 g). The resulting mixture was stirred at ambient temperature for 18 hours. There was a significant amount of precipitate present in the reaction mixture, and it was collected by filtration and washed with 50% aqueous tetrahydrofuran. The combined filtrate and wash were concentrated to remove most of the tetrahydrofuran, and the residue was extracted with chloroform. The organic layers were combined and dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel, eluting with 1/1 hexanes/ethyl acetate, to provide the title compound (0.61 g) with the following physical data.

Workup

  1. filtrationwas collected by filtration
  2. washwashed with 50% aqueous tetrahydrofuran
  3. washThe combined filtrate and wash
  4. concentrationwere concentrated
  5. customto remove most of the tetrahydrofuran
  6. extractionthe residue was extracted with chloroform
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by chromatography on silica gel
  10. washeluting with 1/1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-bf6916386b1042578a10b049327b3444
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

Loading…