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

HRID 1582103Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1582103
[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 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 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-68bc5d73fe5f42508c8cd2b1b6f0b42f
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06734179B2

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