Oxalyl chloride → 2,4-Difluorophenylacetyl chloride

HRID 36922

Reaktionsgleichung

Reaktionsgleichung von HRID 36922
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([OH:12])=O.C(Cl)(=O)C([Cl:16])=O>CN(C=O)C.O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([Cl:16])=[O:12]

Komponenten

5

Edukt 2

HCID 65578Oxalyl chlorideHCID 1235812,4-Difluorophenylacetic acid

Produkt 1

HCID 152316062,4-Difluorophenylacetyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 2,4-difluorophenylacetic acid (206 mg), DMF (1 drop) and tetrahydrofuran (4 ml) was added oxalyl chloride (0.13 ml) dropwise. The resulting mixture was stirred at room temperature for 1 hour and the solvent was then distilled off to give 2,4-difluorophenylacetyl chloride. This chloride was dissolved in dichloromethane (5 ml) followed by addition of 3-amino-4-(2-chlorophenyl)-7,8-dihydro-6H-cyclopenta[g]quinoline (294 mg) and N,N-dimethylaniline (0.13 ml). The mixture was further stirred at room temperature for 3 hours, after which it was washed with water, saturated aqueous solution of NaHCO3 and water in the order mentioned and dried (over MgSO4). The solvent was then distilled off to give 4-(2-chlorophenyl)-3-(2,4-difluorophenylacetylamino)-7,8-dihydro-6H-cyclopenta(g)quinoline as oil. This oil was crystallized from isopropyl ether (yield 342 mg, 76.3%). Recrystallization from ethanol gave colorless prisms, mp. 179°-180° C.

Aufarbeitung

  1. distillationthe solvent was then distilled off

Quellen und Nachweise

ORD-Eintrag
ord-7136b0aec2a94decbecda8f435272e8f
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05418239

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