Benzonitrile, m-chloro- → 3-Chlorobenzamidoxime

HRID 732105

Reaktionsgleichung

Reaktionsgleichung von HRID 732105
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].Cl.[NH2:11][OH:12].[OH-].[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:5](=[N:11][OH:12])[NH2:6])[CH:7]=[CH:8][CH:9]=1

Komponenten

6

Edukt 3

HCID 13015Benzonitrile, m-chloro-HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochloride

Produkt 1

HCID 27948173-ChlorobenzamidoximeAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A solution of 3.35 mL (30.0 mmol) 3-chlorobenzonitrile in ethanol (40 mL) was added to a solution of 2.47 g (35.5 mmol) hydroxylamine hydrochloride and 1.42 g (35.5 mmol) NaOH in water (20 mL) at r.t. and then heated at 90° C. for 24 h. After cooling, the reaction mixture was concentrated, the residue diluted with water, followed by filtration and drying to afford 1.13 g (93%) of the title compound. 1H NMR: 8.11 (s, 1H), 7.72 (s, 1H), 7.61 (m, 1H), 7.46 (m, 1H), 7.36 (m, 1H).

Aufarbeitung

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated
  3. additionthe residue diluted with water
  4. filtrationfollowed by filtration
  5. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-984eed0d5b914057b9a2f2df9a258a65
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585881B2

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