Hydroxylamine HCl → 2-Chloro-3-hydroxybenzonitrile

HRID 225821

Reaktionsgleichung

Reaktionsgleichung von HRID 225821
[Cl:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[Cl-].O[NH3+:13]>C(O)(=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:13]

Komponenten

5

Edukt 2

HCID 21645Hydroxylamine HClHCID 5933762-Chloro-3-hydroxybenzaldehyde

Produkt 1

HCID 214365452-Chloro-3-hydroxybenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 2-chloro-3-hydroxybenzaldehyde [(2 g, 12.8 mmol) WO 2005007633, p34] and hydroxyl ammonium chloride (1.33 g, 19.6 mmol) in acetic acid (20 mL) was heated under reflux for 2 hours. The reaction mixture was then cooled to room temperature and partitioned between diethyl ether and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and concentrated in vacuo to give a white solid. The solid was then dissolved in ethyl acetate washed with water and brine, dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a solid in quantitative yield.

Aufarbeitung

  1. temperatureunder reflux for 2 hours
  2. custompartitioned between diethyl ether and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a white solid
  8. washwashed with water and brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ada5673d3bfe4b2b954acd2604a1bd63
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557131B2

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