Hydrazine hydrate (1:1) → o-(4-Chlorophenyl)hydroxylamine

HRID 1697442Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1697442
O.NN.[Cl:4][C:5]1[CH:22]=[CH:21][C:8]([O:9][N:10]2C(=O)C3=CC=CC=C3C2=O)=[CH:7][CH:6]=1>C(Cl)(Cl)Cl.CO>[Cl:4][C:5]1[CH:22]=[CH:21][C:8]([O:9][NH2:10])=[CH:7][CH:6]=1

Komponenten

5

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 153707352-(4-Chlorophenoxy)isoindoline-1,3-dione

Produkt 1

HCID 12571735o-(4-Chlorophenyl)hydroxylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Hydrazine hydrate (0.56 mL, 12 mmol) was added to a solution of Example 3A (820 mg, 3.0 mmol) in chloroform (37 mL) and methanol (4 mL). The suspension was stirred at room temperature for 22 hours. Silica gel (10 g) was added, and the mixture was concentrated to dryness. The residue was applied to the top of a flash chromatography column and eluted with hexanes-ethyl acetate (80:20) to provide the title compound as the free amine. The residue was dissolved in ethanol (5 mL) and treated with HCl/dioxane (4M, 1 mL). The solution was heated at reflux and diluted with gradual addition of ethyl acetate (50 mL). The mixture was cooled to room temperature and filtered to provide the title compound as a hydrochloride salt. 1H NMR (300 MHz, CD3OD) δ 7.15-7.22 (m, 2 H), 7.42-7.49 (m, 2 H).

Aufarbeitung

  1. additionSilica gel (10 g) was added
  2. concentrationthe mixture was concentrated to dryness
  3. washeluted with hexanes-ethyl acetate (80:20)

Quellen und Nachweise

ORD-Eintrag
ord-d5b0d20dac0849c6ae4cb41d7105fad4
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163915B2

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