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

HRID 393660노트

반응식

HRID 393660 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-58ff0d3da07b4ee3942f9b67e49657a4
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809097B1

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