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

HRID 1042249

反応式

HRID 1042249 の反応式
[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

参加物

5

反応物 2

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

生成物 1

HCID 596273751-Chloro-6-methylisoquinolin-5-amine収率 40.4%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 21584144Dichloromethane ethanol溶媒

反応条件

温度
70 °C

実験手順

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]+

後処理

  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)

出典と根拠

ORDレコード
ord-d8de82e3eeb9429bb135be4b66ab8ddd
出典データセット
uspto-grants-2013_10
特許番号
US08557830B2

関連ノート

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