Pyridine → 4-(Dimethylamino)-3-(2-nitrophenyl)but-3-en-2-one

HRID 1579544Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1579544
[CH3:1][N:2]([CH3:14])[CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12].N1C=CC=CC=1.[C:21](Cl)(=[O:23])[CH3:22]>CCOCC>[C:21]([C:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12])=[CH:3][N:2]([CH3:1])[CH3:14])(=[O:23])[CH3:22]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 54442712N,N-Dimethyl-2-(2-nitrophenyl)ethen-1-amine

Produkt 1

HCID 541295954-(Dimethylamino)-3-(2-nitrophenyl)but-3-en-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 3.84 g. of β-dimethylamino-2-nitrostyrene and 1.61 ml. of pyridine in 20 ml. of ether, was added dropwise a solution of 1.42 ml. of acetyl chloride in 5 ml. of ether. The mixture was stirred for 3 hours at 0° and filtered. The gummy solid was partitioned between methylene chloride and water. The organic phase was washed with dilute hydrochloride, dried and concentrated to a dark oil. The nmr spectrum was in agreement with the proposed structure. This product, i.e., α-acetyl-β-dimethylamino-2-nitrostyrene was used without further purification in the next step.

Aufarbeitung

  1. filtrationfiltered
  2. customThe gummy solid was partitioned between methylene chloride and water
  3. washThe organic phase was washed with dilute hydrochloride
  4. customdried
  5. concentrationconcentrated to a dark oil
  6. customThis product, i.e., α-acetyl-β-dimethylamino-2-nitrostyrene was used without further purification in the next step

Quellen und Nachweise

ORD-Eintrag
ord-7f42447333b94553846c9dd46429a419
Quelldatensatz
uspto-grants-1976_01
Patentnummer
US03931225

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