Acetic Acid → Ethyl 5,7-dichloro-8-methoxyquinoline-3-carboxylate

HRID 1436965Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1436965
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[C:13]([Cl:17])[CH:12]=[C:11]([Cl:18])[C:10]=2[O:19][CH3:20])=[O:5])[CH3:2].C(O)(=O)C.C(OCC)(=O)C>O1CCOCC1.[Zn]>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[C:13]([Cl:17])[CH:12]=[C:11]([Cl:18])[C:10]=2[O:19][CH3:20])=[O:5])[CH3:2]

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 57939336Ethyl 4,5,7-trichloro-8-methoxyquinoline-3-carboxylate

Produkt 1

HCID 57939343Ethyl 5,7-dichloro-8-methoxyquinoline-3-carboxylateAusbeute 39,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A suspension of zinc powder (0.70 g) was stirred at 20° C. in a solution of 4,5,7-trichloro-8-methoxy-quinoline-3-carboxylic acid ethyl ester 26 (364 mg, 1.09 mmol) and acetic acid (2.2 ml) in 1,4-dioxane (15 ml). After 20 minutes, ethyl acetate (20 ml) was added and the resultant mixture filtered through a pad of celite. The filtrate was washed with saturated aqueous sodium chloride solution (10 ml), dried (MgSO4), filtered, and the solvent removed under vacuum. The residue was chromatographed on flash silica (ethyl acetate/hexane, 1:9), yielding 130 mg (39%) of the title compound 27 as a white solid. 1H NMR (CDCl3, 400 MHz): δ 9.51 (d, J=2.0, 1 H), 9.15 (d, J=2.0, 1 H), 7.72 (s, 1H), 4.51 (q, J=7.2, 2 H), 4.18 (s, 3H), 1.47 (t, J=7.2, 3 H).

Aufarbeitung

  1. filtrationthe resultant mixture filtered through a pad of celite
  2. washThe filtrate was washed with saturated aqueous sodium chloride solution (10 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent removed under vacuum
  6. customThe residue was chromatographed on flash silica (ethyl acetate/hexane, 1:9)

Quellen und Nachweise

ORD-Eintrag
ord-0e127a599cdd4f578ea71bdd1e916dd0
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07619091B2

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