Hydrochloric Acid → 2-Amino-6-difluoromethoxy-benzonitrile

HRID 39221

Reaktionsgleichung

Reaktionsgleichung von HRID 39221
[F:1][CH:2]([F:15])[O:3][C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-])=O)[C:5]=1[C:6]#[N:7].[Sn](Cl)Cl.Cl.[OH-].[Na+]>C(O)(C)C.O>[NH2:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:4]([O:3][CH:2]([F:1])[F:15])[C:5]=1[C:6]#[N:7]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 581007642-Difluoromethoxy-6-nitrobenzonitrile

Produkt 1

HCID 581007652-Amino-6-difluoromethoxy-benzonitrileAusbeute 121 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

To a solution of 2-difluoromethoxy-6-nitro-benzonitrile (4.0 g, 14.9 mmol) (Example I3) in isopropanol (100 ml) is added tin(II) chloride (10.2 g, 53.6 mmol). Aqueous hydrochloric acid (concentrated) (14.4 ml) is added slowly and the reaction mixture is heated to reflux for 30 minutes. The reaction mixture is cooled to room temperature, diluted with water and the pH is adjusted to 10 by addition of NaOH (2M). The mixture is extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulfate and concentrated to yield 2-amino-6-difluoromethoxy-benzonitrile (3.32 g, 93% yield) in pure form. 1H-NMR (CDCl3, 400 MHz): 7.05 (t, 1H), 6.65 (d, 1H), 6.55 (t, 1H), 6.50 (t, 1H), 4.25 (s, br, 2H) ppm.

Aufarbeitung

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux for 30 minutes
  3. extractionThe mixture is extracted three times with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-17568dea09934574afe97a0723533b5e
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524896B2

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