2-Chloronicotinoyl chloride → HCID 18436872, Verbindung

HRID 456619Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 456619
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([C:11]2[CH:15]=[CH:14][NH:13][CH:12]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl:16][C:17]1[N:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19](Cl)=[O:20]>C(Cl)Cl.C(OCC)(=O)C>[Cl:16][C:17]1[C:18]([C:19]([C:12]2[NH:13][CH:14]=[CH:15][C:11]=2[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:20])=[CH:22][CH:23]=[CH:24][N:25]=1

Komponenten

6

Edukt 3

HCID 27745412-Chloronicotinoyl chlorideHCID 53241103-phenyl-1H-pyrroleHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 18436872HCID 18436872, VerbindungAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Aluminum chloride (1.33 g, 10 mmol) was added to a mixture of 3-phenyl-1H-pyrrole (1.35 g, 9.4 mmol, prepared as described in Journal of Organic Chemistry, 62: 2650 (1997) (incorporated herein by reference) and 2-chloronicotinoyl chloride (1.65 g, 9.4 mmol) in DCM (15 mL) at 0° C. The mixture was stirred at 0° C. for 30 mins and at room temperature for one hour. The reaction was diluted with ethyl acetate and washed with brine, 2N NaOH, brine, dried and concentrated. The residue was purified on silica gel column to give 0.682 g (26%) of (2-chloro-pyridin-3-yl)-(3-phenyl-1H-pyrrol-2-yl)-methanone.

Aufarbeitung

  1. customprepared
  2. customat 0° C
  3. washwashed with brine, 2N NaOH, brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-f4d4b40ed8c845d1934b03128835c46a
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186716B2

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