4-Chloroaniline → 3-Chloropyruvaldehyde 4-chlorophenylhydrazone

HRID 1632165

Reaktionsgleichung

[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[N:9]([O-])=O.[Na+].[Cl:13][CH2:14]C(=O)CC(O)=O.[C:21]([O-:24])(=O)[CH3:22].[Na+]>O.Cl>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][N:9]=[C:22]([CH2:14][Cl:13])[CH:21]=[O:24])=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

In a mixture of 500 ml of water and 250 ml of concentrated hydrochloric acid is dissolved 128 g of p-chloroaniline. To this solution is added dropwise a solution of 69 g of sodium nitrite in 100 ml of water, while the reaction temperature is maintained at 0° C. Then, to the reaction mixture is added a solution of 136.5 g of 4-chloroacetoacetic acid in 200 ml of water, while the reaction temperature is maintained within the range from 0° C. to 5° C., followed by further addition of a solution of 164 g of sodium acetate in 300 ml of water, whereupon yellow precipitate is produced while bubbling vigorously. The reaction mixture is stirred at a room temperature until the bubbling ceases, followed by collecting the crystals by filtration, washing with water and drying, whereby 224 g of the subject compound is obtained. Yield 97%. m.p. 190° C.-192° C. (decomp.)

Aufarbeitung

temperaturewhile the reaction temperature is maintained within the range from 0° C. to 5° C.
customis produced
customwhile bubbling vigorously
customby collecting the crystals
filtrationby filtration
washwashing with water
customdrying

Quellen und Nachweise

ORD-Eintrag: ord-17c20047165c408db3bc596c01e7cbc1
Quelldatensatz: uspto-grants-1984_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04474775

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