Hydrochloric Acid → Ethyl 2-(3-chloro-4-fluoro-phenylhydrazino)propionate

HRID 544921

Reaktionsgleichung

Reaktionsgleichung von HRID 544921
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].Cl.[N:11]([O-])=O.[Na+].[CH3:15][CH:16](C(C)=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18].[OH-].[K+].C([O-])(=O)C.[Na+]>O.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][NH:11][CH:16]([CH3:15])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:6]=[CH:7][C:8]=1[F:9]

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 701Ethyl 2-methylacetoacetateHCID 97083-Chloro-4-fluoroanilineHCID 14797Potassium HydroxideHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Produkt 1

HCID 67197345Ethyl 2-(3-chloro-4-fluoro-phenylhydrazino)propionateAusbeute 34,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 3-chloro-4-fluoroaniline (10.0 g) in a 6 N aqueous hydrochloric acid solution (35 ml) was cooled to 0° C., and thereto was added dropwise a solution of sodium nitrite (4.80 g) in H2O (6.3 ml). After being stirred at same temperature for 25 minutes, the mixture was added to a solution of ethyl 2-methylacetoacetate (11.0 g), potassium hydroxide (21.2 g) and sodium acetate (21.2 g) in ethyl alcohol (80 ml)-H2O (100 ml) in one portion at 0° C. The resultant mixture was stirred at same temperature for 2 hours, and extracted with diethyl ether. The organic layer was washed with water twice and brine followed by being dried over sodium sulfate. The insoluble materials were filtered off, and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1-3:1) to give ethyl 2-(3-chloro-4-fluoro-phenylhydrazino)propionate (6.16 g) as a reddish solid. APCI-Mass m/Z 259/261 (M+H).

Aufarbeitung

  1. extractionextracted with diethyl ether
  2. washThe organic layer was washed with water twice
  3. dry with materialby being dried over sodium sulfate
  4. filtrationThe insoluble materials were filtered off
  5. customthe filtrate was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1-3:1)

Quellen und Nachweise

ORD-Eintrag
ord-0a179adff3f141c2962997c3878a5082
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935674B2

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