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

HRID 1042249

Reaktionsgleichung

Reaktionsgleichung von HRID 1042249
[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

Komponenten

5

Edukt 2

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

Produkt 1

HCID 596273751-Chloro-6-methylisoquinolin-5-amineAusbeute 40,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 21584144Dichloromethane ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

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]+

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-d8de82e3eeb9429bb135be4b66ab8ddd
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557830B2

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