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1,2-Dimethoxyethane → 1-(5-Chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-7-ylamine

HRID 1715854
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1715854
[Cl-].[NH4+].COCCOC.[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([O:32][CH3:33])=[C:14]([S:16]([N:19]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([N+:29]([O-])=O)[CH:27]=3)[CH2:22][CH2:21][CH2:20]2)(=[O:18])=[O:17])[CH:15]=1>O.[Zn]>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([O:32][CH3:33])=[C:14]([S:16]([N:19]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([NH2:29])[CH:27]=3)[CH2:22][CH2:21][CH2:20]2)(=[O:17])=[O:18])[CH:15]=1
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Komponenten

6

Edukt 3

HCID 80711,2-DimethoxyethaneHCID 25517Ammonium ChlorideHCID 684327391-(5-Chloro-2-methoxy-benzenesulfonyl)-7-nitro-1,2,3,4-tetrahydro-quinoline

Produkt 1

HCID 684327061-(5-Chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-7-ylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysator
HCID 962
Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
15 °C

Versuchsvorschrift

A 27% solution of ammonium chloride in water (35.00 mL) was mixed with 1,2-dimethoxyethane (21.00 mL) and the mixture cooled to 15° C. 1-(5-Chloro-2-methoxy-benzenesulfonyl)-7-nitro-1,2,3,4-tetrahydro-quinoline (1.00 g, 26.10 mmol) was added under vigorous stirring, followed by zinc powder (2.22 g, 33.96 mmol). The mixture was warmed to room temperature and stirred for 1 hour. After filtering off the solids, the organic solvent was evaporated and the residual slurry extracted several times with ethyl acetate. The combined organic phases were dried over magnesium sulphate and evaporated. The residue was purified by flash chromatography (dichloromethane/methanol gradient) to yield 1-(5-chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-7-ylamine as a brown solid, 0.32 g (35%), MS (ISP): m/e=353.2 (M+H).

Aufarbeitung

  1. temperatureThe mixture was warmed to room temperature
  2. filtrationAfter filtering off the solids
  3. customthe organic solvent was evaporated
  4. extractionthe residual slurry extracted several times with ethyl acetate
  5. dry with materialThe combined organic phases were dried over magnesium sulphate
  6. customevaporated
  7. customThe residue was purified by flash chromatography (dichloromethane/methanol gradient)

Quellen und Nachweise

ORD-Eintrag
ord-6fc785cbefbf444faa25ebdda12db092
Quelldatensatz
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07799933B2

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