4-(4-methoxy-3-nitro-phenyl)-3,6-dihydro-2H-pyran → 2-Methoxy-5-(tetrahydropyran-4-yl)-phenylamine

HRID 968541Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 968541
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][CH2:11][O:12][CH2:13][CH:14]=2)=[CH:5][C:4]=1[N+:15]([O-])=O>CO.ClCCl.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:5][C:4]=1[NH2:15]

Komponenten

5

Edukt 1

HCID 219192154-(4-methoxy-3-nitro-phenyl)-3,6-dihydro-2H-pyran

Produkt 1

HCID 219192622-Methoxy-5-(tetrahydropyran-4-yl)-phenylamineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 3.30 g (14.0 mmol) 4-(4-methoxy-3-nitro-phenyl)-3,6-dihydro-2H-pyran (VIII) in 70 ml methanol and 70 ml dichloromethane was added a spatula end of 10% palladium on charcoal and the mixture was then stirred for 20 minutes at room temperature under an atmosphere of hydrogen. The mixture was then filtered, washing with dichloromethane, and the filtrate concentrated in vacuo to afford 2.75 g (95%) 2-methoxy-5-(tetrahydro-pyran-4-yl)-phenylamine (IX) as an off-white crystalline solid ES-MS m/e (%): 208 (M+H+, 100).

Aufarbeitung

  1. filtrationThe mixture was then filtered
  2. washwashing with dichloromethane
  3. concentrationthe filtrate concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-665deef74add42a592170ce851ab57dd
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07304058B2

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