Phosphorus oxychloride → 6-Acetamido-4-chloro-[1,5]naphthyridine-3-carbonitrile

HRID 1266276Notes

Reaction equation

HRID 1266276 reaction equation
[C:1]([NH:4][C:5]1[N:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][C:9]([C:15]#[N:16])=[C:8]2O)(=[O:3])[CH3:2].O=P(Cl)(Cl)[Cl:20]>>[C:1]([NH:4][C:5]1[N:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][C:9]([C:15]#[N:16])=[C:8]2[Cl:20])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178474058HCID 178474058, compound

Product 1

HCID 129691036-Acetamido-4-chloro-[1,5]naphthyridine-3-carbonitrileYield 19%

Procedure

A solution of 6-acetamido-4-hydroxyl-[1,5]naphthyridine-3-carbonitrile (1.0 g, 4.386 mmol) was heated at reflux in POCl3 (20 ml) under nitrogen for 5 hrs. After cooling, the solvent was removed by rotary evaporation. Ice water was added to the black residue, which was cooled (ice bath) and stirred for 1 hr. The mixture was warmed to room temperature and stirred at room temperature for 1 hr. The mixture was cooled with ice bath, and made basic with NH4OH. The aqueous layer was extracted with CH2Cl2. The combined extracts were washed with water, dried (Na2SO4) and concentrated to give the title compound as a dark blue solid (200 mg, 19%).

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed by rotary evaporation
  3. additionIce water was added to the black residue, which
  4. temperaturewas cooled (ice bath)
  5. stirringstirred at room temperature for 1 hr
  6. temperatureThe mixture was cooled with ice bath
  7. extractionThe aqueous layer was extracted with CH2Cl2
  8. washThe combined extracts were washed with water
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-fc4f81a8866b44619d0ec1428c0b0724
Source dataset
uspto-grants-2003_04
Patent number
US06548496B2

Reaction notes

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