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

HRID 393660ノート

反応式

HRID 393660 の反応式
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]

参加物

5

反応物 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178474045HCID 178474045、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-58ff0d3da07b4ee3942f9b67e49657a4
出典データセット
uspto-grants-2004_10
特許番号
US06809097B1

反応ノート

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