Phosphorus oxychloride → 1-chloro-7-nitroisoquinoline

HRID 1070464ノート

反応式

HRID 1070464 の反応式
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][N+:10]([O-])=[CH:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].P(Cl)(Cl)([Cl:17])=O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Cl:17][C:11]1[C:12]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=2)[CH:8]=[CH:9][N:10]=1

参加物

5

反応物 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 21862656HCID 21862656、化合物

生成物 1

HCID 218626571-chloro-7-nitroisoquinoline収率 14%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

To a suspension of 7-nitroisoquinoline N-oxide obtained in Preparation Example 1-5, Step 3 in toluene (185 ml) was added phosphorus oxychloride (3.5 ml, 37 mmol), and the mixture was stirred under heating at 90° C. for 2 hr. The reaction mixture was cooled to room temperature and the reaction mixture was poured into an aqueous sodium hydrogencarbonate solution. The aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:acetone=30:1) to give 1-chloro-7-nitroisoquinoline (540 mg, 14%).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform:acetone=30:1)

出典と根拠

ORDレコード
ord-848fa20054324ab49142b0e3bd91b254
出典データセット
uspto-grants-2005_06
特許番号
US06903094B2

反応ノート

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