Stannous Chloride → 1-Chloro-6-methylisoquinolin-5-amine

HRID 1042249

반응식

HRID 1042249 반응식
[Sn](Cl)Cl.[Cl:4][C:5]1[C:14]2[C:9](=[C:10]([N+:16]([O-])=O)[C:11]([CH3:15])=[CH:12][CH:13]=2)[CH:8]=[CH:7][N:6]=1>C(O)C.C(Cl)Cl.C(Cl)Cl>[Cl:4][C:5]1[C:14]2[CH:13]=[CH:12][C:11]([CH3:15])=[C:10]([NH2:16])[C:9]=2[CH:8]=[CH:7][N:6]=1

참가 물질

5

반응물 2

HCID 24479Stannous ChlorideHCID 226222211-Chloro-6-methyl-5-nitroisoquinoline

생성물 1

HCID 596273751-Chloro-6-methylisoquinolin-5-amine수율 40.4%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 21584144Dichloromethane ethanol용매

반응 조건

온도
70 °C

실험 절차

Tin (II) chloride (0.43 g, 2.2 mmol) was added to a solution of 1-chloro-6-methyl-5-nitroisoquinoline (0.100 g, 0.45 mmol) in ethanol/DCM (10.0 mL, 4:1). The solution was heated at 70° C. for 16 h. The reaction mixture was diluted with DCM and the organic phase was washed with saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford a brown solid which was purified via column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-50% ethyl acetate-hexane) to afford 1-chloro-6-methylisoquinolin-5-amine (0.035 g, 40% yield) as a brown solid. MS (ESI, pos. ion) m/z: 193 [M+H]+

후처리

  1. washthe organic phase was washed with saturated aqueous sodium bicarbonate solution and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford a brown solid which
  6. customwas purified via column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-50% ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-d8de82e3eeb9429bb135be4b66ab8ddd
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557830B2

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