Hydrochloric Acid → Ethyl Pyruvate 4-Chloro-3-Fluorophenylhydrazone

HRID 50031

Reaktionsgleichung

Reaktionsgleichung von HRID 50031
[N:1]([O-])=O.[Na+].[Cl:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][C:7]=1[F:13].Cl.C([O-])(=O)C.[K+].[CH3:20][CH:21](C(C)=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23]>O.CO.C(O)C>[Cl:5][C:6]1[CH:12]=[CH:11][C:9]([NH:10][N:1]=[C:21]([CH3:20])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:8][C:7]=1[F:13]

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 701Ethyl 2-methylacetoacetateHCID 517044Potassium Acetate2×HCID 27365114-Chloro-3-fluoroanilineHCID 23668193Sodium Nitrite

Produkt 1

HCID 73115740Ethyl Pyruvate 4-Chloro-3-FluorophenylhydrazoneAusbeute 30,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of sodium nitrite (4.76 g, 0.069 mol) in water (6.3 mL) was added dropwise to an ice cooled mixture of 4-chloro-3-fluoroaniline (J. Am. Chem. Soc., 1996, 61, 5130-5133) (10.00 g, 0.069 mol), water (167 mL) and 37% hydrochloric acid (167 mL). After 20 minutes potassium acetate (9.81 g, 0.10 mol) was added, and then a solution of ethyl 2-methylacetoacetate (9.95 g, 0.069 mol), potassium acetate (9.81 g, 0.10 mol) in methanol (67 mL) was dropped while cooling on the ice bad. Reaction was stirred at 0° C. for 3 hours, then extracted with diethyl ether. Organic layer was washed with brine and dried. Removal of the solvent furnished a red oily residue that was treated with ethanol (100 mL) and stirred at room temperature overnight. The solid which formed was filtered a recrystallized from ethanol to give 5.4 g (30%) of title compound, mp 161-163° C. (from ethanol).

Aufarbeitung

  1. temperaturecooled
  2. customReaction
  3. extractionextracted with diethyl ether
  4. washOrganic layer was washed with brine
  5. customdried
  6. customRemoval of the solvent
  7. customfurnished a red oily residue that
  8. stirringstirred at room temperature overnight
  9. customThe solid which formed
  10. filtrationwas filtered
  11. customa recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-fd12142649ea4bb5af36be8b36b06f39
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710068B2

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