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Acetic Acid → 5-Amino-6-((S)-2-imidazol-1-yl-1-pyridin-3-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one

HRID 496429
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 496429
[N:1]1([CH2:6][C@H:7]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[O:8][C:9]2[C:10]([N+:20]([O-])=O)=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[CH2:14][CH2:13][CH2:12]3)[CH:5]=[CH:4][N:3]=[CH:2]1.CO.C(O)(=O)C.C([O-])(O)=O.[Na+]>[Fe].CCOC(C)=O.O>[NH2:20][C:10]1[C:9]([O:8][C@@H:7]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:18][CH:17]=[C:16]2[C:11]=1[CH2:12][CH2:13][CH2:14][C:15]2=[O:19]
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Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 887MethanolHCID 516892Sodium BicarbonateHCID 697370746-((S)-2-Imidazol-1-yl-1-pyridin-3-yl-ethoxy)-5-nitro-3,4-dihydro-2H-naphthalen-1-one

Produkt 1

HCID 697352345-Amino-6-((S)-2-imidazol-1-yl-1-pyridin-3-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-oneAusbeute 46,6 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 23925IronKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 6-((S)-2-Imidazol-1-yl-1-pyridin-3-yl-ethoxy)-5-nitro-3,4-dihydro-2H-naphthalen-1-one (1.60 g, 4.23 mmol), MeOH (85 mL), H2O (19 mL) and glacial acetic acid (2.4 mL, 42 mmol) was treated at reflux with iron powder (2.34 g, 42 mmol). The reaction was monitored by mass spectrometry and was complete in 4 h. The volume of solvent was reduced under reduced pressure. EtOAc and dilute aqueous NaHCO3 were added. A brownish-green emulsion formed which was filtered through Celite. The mixture was extracted with EtOAc. The combined organic layer was washed with dilute aqueous NaHCO3 and brine, dried over Na2SO4, and concentrated under reduced pressure to give an off-white foam (0.685 g, 1.97 mmol, 46%). The structure was confirmed by NMR and mass spectrometry. MS m/z 349 (M++H).

Aufarbeitung

  1. additionwas treated
  2. customA brownish-green emulsion formed which
  3. filtrationwas filtered through Celite
  4. extractionThe mixture was extracted with EtOAc
  5. washThe combined organic layer was washed with dilute aqueous NaHCO3 and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6e1990f2a90e4710b89d79cebe27b6ce
Quelldatensatz
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06943183B2

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