3-(Trifluoromethyl)aniline → HCID 178501727, Verbindung

HRID 1805436Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1805436
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[N:12]([O-])=O.[Na+].[C:16]([O:22][CH3:23])(=[O:21])[CH2:17][C:18]([CH3:20])=[O:19].C([O-])(=O)C.[Na+]>Cl.O.C(O)C>[O:19]=[C:18]([CH3:20])[C:17](=[N:12][NH:6][C:5]1[CH:7]=[CH:8][CH:9]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=1)[C:16]([O:22][CH3:23])=[O:21]

Komponenten

8

Edukt 4

HCID 73753-(Trifluoromethyl)anilineHCID 7757Methyl acetoacetateHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Produkt 1

HCID 178501727HCID 178501727, VerbindungAusbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A slurry of 3-(trifluoromethyl)aniline (16.12 g, 100 mmol) in 6 N HCl (100 mL) was cooled to 0° C. and treated dropwise with a solution of sodium nitrite (8.33 g, 121 mmol) in water (20 mL). The resulting pale yellow solution was poured into a slurry of methyl acetoacetate (11.62 g, 100 mmol) and sodium acetate (150 g) in ethanol (170 mL), pre-cooled to 0° C. The resulting orange slurry was stirred for 10 min. After that time, the product was collected by filtration and washed with water (500 mL). The crude material was dissolved in ethyl acetate (250 mL) and dried (MgSO4). The product crystallized upon concentration of the ethyl acetate to give 19.997 g (69%) of methyl 3-oxo-2-{[3-(trifluoromethyl)phenyl]hydrazono}butanoate as light yellow crystals.

Aufarbeitung

  1. filtrationAfter that time, the product was collected by filtration
  2. washwashed with water (500 mL)
  3. dissolutionThe crude material was dissolved in ethyl acetate (250 mL)
  4. dry with materialdried (MgSO4)
  5. customThe product crystallized upon concentration of the ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-0134115095f840afb0abbb012f98c59d
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354411B2

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