N,N-Dimethylaniline → N-(5-chloro-1,8-naphthyridin-2-yl)acetamide

HRID 393660Notes

Reaction equation

HRID 393660 reaction equation
P(Cl)(Cl)([Cl:3])=O.[C:6]([NH:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[N:13][CH:14]=[CH:15][C:16]=2O)[N:11]=1)(=[O:8])[CH3:7].CN(C)C1C=CC=CC=1>C1(C)C=CC=CC=1>[C:6]([NH:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[N:13][CH:14]=[CH:15][C:16]=2[Cl:3])[N:11]=1)(=[O:8])[CH3:7]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178474045HCID 178474045, compound

Product 1

HCID 22646664N-(5-chloro-1,8-naphthyridin-2-yl)acetamideYield 18%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Phosphorous oxychloride (6.0 ml) was added to a stirred mixture of 2-acetamido-5-hydroxy-1,8-naphthyridine (2.4 g, 11.8 mmol) and N,N-dimethylaniline (6.0 ml) in toluene (100 ml). The mixture was then heated at reflux for 1 hour. The mixture was allowed to cool, the tolulene was removed by evaporation and the residue was partitioned between methylene chloride and aqueous sodium hydrogen carbonate solution. The organic layer was separated, dried (MgSO4) and the solvent was removed by evaporation to give 2-acetamido-5-chloro-1,8-naphthyridine (470 mg, 18%) as a brown solid.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 1 hour
  3. temperatureto cool
  4. customthe tolulene was removed by evaporation
  5. customthe residue was partitioned between methylene chloride and aqueous sodium hydrogen carbonate solution
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-58ff0d3da07b4ee3942f9b67e49657a4
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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