Benzoyl chloride → 1-Benzoyl-6-chloro-1,2-dihydroquinoline-2-carbonitrile

HRID 1585573Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1585573
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C[Si]([C:25]#[N:26])(C)C>C(Cl)Cl.[Al+3].[Cl-].[Cl-].[Cl-]>[C:12]([N:8]1[C:9]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]1[C:25]#[N:26])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

6

Edukt 3

HCID 7412Benzoyl chlorideHCID 691636-ChloroquinolineHCID 82115Trimethylsilyl cyanide

Produkt 1

HCID 133367791-Benzoyl-6-chloro-1,2-dihydroquinoline-2-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6451240Aluminum(III) ChlorideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 6-chloroquinoline (9.5 g), benzoyl chloride (13.2 g) in methylene chloride (50 mL) was treated with AlCl3 (0.10 g) followed by dropwise addition of trimethyl silyl cyanide (12.5 mL). After 0.5 hour, the mixture was diluted with 150 mL of methylene chloride and washed with water, 1N HCl, saturated sodium bicarbonate (aq.), and brine. The organic phase was dried over magnesium sulfate then evaporated to dryness. The residue was purified by column chromatography on silica gel using ethyl acetate/hexane (3:7) as the eluting solvent. The title compound (13 g) was obtained as a white solid, m.p. 141-143° C. This product was used for the preparation of the title compound described in step 2.

Aufarbeitung

  1. washwashed with water, 1N HCl, saturated sodium bicarbonate (aq.), and brine
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customthen evaporated to dryness
  4. customThe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-b28014d7ac24484e83c9b1f972a3472e
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05939435

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