Stannous Chloride → 4-Chloro-5-(trifluoromethyl)benzene-1,2-diamine

HRID 54371

Reaktionsgleichung

Reaktionsgleichung von HRID 54371
[NH2:1][C:2]1[CH:3]=[C:4]([C:12]([F:15])([F:14])[F:13])[C:5]([Cl:11])=[CH:6][C:7]=1[N+:8]([O-])=O.Cl[Sn]Cl>C(O)C>[NH2:1][C:2]1[CH:3]=[C:4]([C:12]([F:15])([F:13])[F:14])[C:5]([Cl:11])=[CH:6][C:7]=1[NH2:8]

Komponenten

4

Edukt 2

HCID 24479Stannous ChlorideHCID 27376454-Chloro-2-nitro-5-(trifluoromethyl)aniline

Produkt 1

HCID 27734974-Chloro-5-(trifluoromethyl)benzene-1,2-diamineAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a stirred mixture of 3-amino-6-chloro-4-nitrobenzotrifluoride (300 mg, 1.25 mmol) in ethanol (5 mL) was added SnCl2 ·2 H2O (1.40 g, 6.20 mmol) in one portion. The mixture was refluxed at 80° C. (oil bath, 90° C.) for 1 h and the solution was cooled to room temperature and ice water (20 g) was added. It was adjusted to pH=7 and extracted with ethyl acetate. The extract was dried over Mg2SO4 and evaporated to give 185 mg (71%) of 3,4-diamino-6-chlorobenzotrifluoride as a brown solid. 1H NMR (CDCl3): δ3.404 (s, 2H); 3.717 (s, 2H); 6.754 (s, 1H); 6.974 (s, 1H).

Aufarbeitung

  1. temperaturethe solution was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over Mg2SO4
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-9a4e5912b3e34bdd83f7a1151a3a2f53
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622952

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