5-(6-Benzyloxy-3,4-dihydronaphthalen-2-yl)-6-nitrobenzo[1,3]dioxole → 6-(6-Aminobenzo[1,3]dioxole-5-yl)-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 2423692Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2423692
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C:19]1[C:27]([N+:28]([O-])=O)=[CH:26][C:22]3[O:23][CH2:24][O:25][C:21]=3[CH:20]=1)[CH2:13][CH2:12]2)C1C=CC=CC=1>C(O)(=O)C.[OH-].[Pd+2].[OH-]>[NH2:28][C:27]1[C:19]([CH:14]2[CH2:13][CH2:12][C:11]3[CH:10]=[C:9]([OH:8])[CH:18]=[CH:17][C:16]=3[CH2:15]2)=[CH:20][C:21]2[O:25][CH2:24][O:23][C:22]=2[CH:26]=1

Komponenten

4

Edukt 1

HCID 666270645-(6-Benzyloxy-3,4-dihydronaphthalen-2-yl)-6-nitrobenzo[1,3]dioxole

Produkt 1

HCID 230874786-(6-Aminobenzo[1,3]dioxole-5-yl)-5,6,7,8-tetrahydronaphthalen-2-olAusbeute 40,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 5-(6-benzyloxy-3,4-dihydronaphthalen-2-yl)-6-nitrobenzo[1,3]dioxole (832 mg) in acetic acid (10 ml) was added 20% palladium hydroxide-activated charcoal (200 mg), and the solution was stirred for 13 hours at room temperature under a hydrogen atmosphere at 4 atmospheric pressures. After filtration through celite pad, the solution was concentrated, neutralized with aqueous ammonia, extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (240 mg).

Aufarbeitung

  1. filtrationAfter filtration through celite pad
  2. concentrationthe solution was concentrated
  3. extractionextracted with ethyl acetate
  4. washsequentially washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system)

Quellen und Nachweise

ORD-Eintrag
ord-30555c0777e64a239a1d81f30e79b854
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960412B2

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