Methanol → 2-(5-(3,4-Dichlorophenyl)furan-2-yl)ethanamine hydrochloride

HRID 872430

Reaktionsgleichung

Reaktionsgleichung von HRID 872430
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[O:10][C:11](/[CH:14]=[CH:15]/[N+:16]([O-])=O)=[CH:12][CH:13]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].CO.Cl.CO>[Pd].C(OCC)(=O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[O:10][C:11]([CH2:14][CH2:15][NH2:16])=[CH:12][CH:13]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 8976012-(3,4-Dichlorophenyl)-5-(2-nitrovinyl)furan2×HCID 21893726Hydrochloride methanol

Produkt 1

HCID 671683442-(5-(3,4-Dichlorophenyl)furan-2-yl)ethanamine hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-(3,4-Dichlorophenyl)-5-((E)-2-nitrovinyl)furan (5.73 g, 20.2 mmol) was dissolved into the mixture of dry methanol (90 ml) and dry ethyl acetate (70 ml). Then, 14.3 ml of 10 w-% HCl-methanol and 2.4 g of 10% palladium on carbon were added. 2-(3,4-Dichlorophenyl)-5-((E)-2-nitrovinyl)furan was hydrogenated at 3 atm at RT for about 4 h. The catalyst was removed by filtrating through Celite®. Removal of solvent under reduced pressure gave a raw product which was purified by flash chromatography on silica gel using CH2Cl2/MeOH (98:2-80:20) as a gradient eluent. 1H NMR (400 MHz, DMSO-d6): 3.04 (2H, m), 3.14 (2H, m), 6.43 (1H, d), 7.07 (1H, d), 7.67 (2H, s), 7.93 (1H, s), 8.19 (3H, broad s).

Aufarbeitung

  1. customThe catalyst was removed
  2. filtrationby filtrating through Celite®
  3. customRemoval of solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-27feb961ce714c799f31d952ece44963
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975254B2

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