Phosphorus oxychloride → 1-Chloro-6-methyl-5-nitroisoquinoline

HRID 1042247ノート

反応式

HRID 1042247 の反応式
P(Cl)(Cl)([Cl:3])=O.[CH3:6][C:7]1[C:8]([N+:18]([O-:20])=[O:19])=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[N+:12]([O-])[CH:11]=[CH:10]2>ClCCCl>[Cl:3][C:13]1[C:14]2[C:9](=[C:8]([N+:18]([O-:20])=[O:19])[C:7]([CH3:6])=[CH:16][CH:15]=2)[CH:10]=[CH:11][N:12]=1

参加物

4

反応物 2

HCID 24813Phosphorus oxychlorideHCID 673410166-Methyl-5-nitroisoquinoline 2-oxide

生成物 1

HCID 226222211-Chloro-6-methyl-5-nitroisoquinoline収率 86%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
70 °C

実験手順

Phosphorous oxychloride (2.15 mL, 23.0 mmol) was added dropwise to a solution of 6-methyl-5-nitroisoquinoline N-oxide (0.940 g, 4.60 mmol) in 1,2-dichloroethane (40.0 mL). The mixture was heated to 70° C. for 3 h to afford an off-white suspension. The mixture was concentrated and the residue was partitioned between dichloromethane and water. The aqueous phase was separated and extracted with dichloromethane. The combined organic phases were washed with saturated aqueous sodium bicarbonate solution, brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford 1-chloro-6-methyl-5-nitroisoquinoline (0.880 g, 86% yield) as an off-white solid. MS (ESI, pos. ion) m/z: 223.0 [M+H]+

後処理

  1. customto afford an off-white suspension
  2. concentrationThe mixture was concentrated
  3. customthe residue was partitioned between dichloromethane and water
  4. customThe aqueous phase was separated
  5. extractionextracted with dichloromethane
  6. washThe combined organic phases were washed with saturated aqueous sodium bicarbonate solution, brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-98839fdd95d54b03b9e0394786066959
出典データセット
uspto-grants-2013_10
特許番号
US08557830B2

反応ノート

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