Sodium Carbonate → 8-Amino-1-tetralone

HRID 28720

Reaktionsgleichung

Reaktionsgleichung von HRID 28720
[O:1]=[C:2]1[C:11]2[C:10]([NH:12]C(=O)C)=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.C([O-])([O-])=O.[Na+].[Na+].[OH-].[Na+]>Cl>[NH2:12][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[C:2](=[O:1])[CH2:3][CH2:4][CH2:5]2

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 12119265N-(8-Oxo-5,6,7,8-tetrahydronaphthalen-1-YL)acetamide

Produkt 1

HCID 114009428-Amino-1-tetraloneAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

The amide (Intermediate J2, 4.12 g, 20.3 mmol) was heated at 90° C. in 6N HCl (140 mL) for 3 h. The mixture was cooled to rt and Na2CO3 was added in small portions followed by addition of 2N NaOH until the mixture was at pH 8. The aqueous layer was extracted with EtOAc and the organic fractions were combined, washed with brine, dried, filtered and concentrated to give 8-amino-3,4-dihydro-2H-naphthalen-1-one (Intermediate J3) as a dark red solid 1.82 g (56%).

Aufarbeitung

  1. extractionThe aqueous layer was extracted with EtOAc
  2. washwashed with brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d4ee0d53e18d4ca895631cd50a28c647
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419994B2

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