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

HRID 1042247노트

반응식

HRID 1042247 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 226222211-Chloro-6-methyl-5-nitroisoquinoline수율 86%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

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온도
70 °C

실험 절차

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]+

후처리

  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

출처 및 근거

ORD 기록
ord-98839fdd95d54b03b9e0394786066959
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557830B2

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