Ethanol → 6-methyl-N1-(3-(trifluoromethyl)phenyl)isoquinoline-1,5-diamine

HRID 1051271

Reaktionsgleichung

Reaktionsgleichung von HRID 1051271
[CH3:1][C:2]1[C:3]([N+:23]([O-])=O)=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1)=[N:7][CH:6]=[CH:5]2.C(O)C.[Sn](Cl)(Cl)(Cl)Cl>C(OCC)(=O)C>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:20])[F:21])[CH:14]=3)=[N:7][CH:6]=[CH:5][C:4]=2[C:3]=1[NH2:23]

Komponenten

5

Edukt 3

HCID 702EthanolHCID 24287Tin tetrachlorideHCID 673394766-Methyl-5-nitro-N-(3-(trifluoromethyl)phenyl)isoquinolin-l-amine

Produkt 1

HCID 444789036-methyl-N1-(3-(trifluoromethyl)phenyl)isoquinoline-1,5-diamineAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

6-Methyl-5-nitro-N-(3-(trifluoromethyl)phenyl)isoquinoline-1-amine (1.49 g, 4.29 mmol) obtained in Step (1) above was stirred in a solvent of ethanol (10 mL). The reaction solution was added with tin chloride (II) dihydrate (4.06 g, 21.46 mmol), and stirred for about 5 hours at 90° C. The reaction mixture was diluted with ethyl acetate, and washed with a saturated aqueous sodium bicarbonate solution and saline. The organic layer thus obtained was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound (0.42 g, 31%).

Aufarbeitung

  1. washwashed with a saturated aqueous sodium bicarbonate solution and saline
  2. customThe organic layer thus obtained
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c58953cc22b8441388a9dd5c6cb91e2f
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388165B2

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