Hydrochloric Acid → 2-(Hydroxyimino)-N-(2-iodophenyl)acetamide

HRID 2375514Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2375514
[NH:1]1C2C(=CC=CC=2)[C:4](=[O:5])[C:2]1=O.Cl.NO.S([O-])([O-])(=O)=O.[Na+].[Na+].Cl.[I:23][C:24]1[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=1[NH2:26].ClC(Cl)(Cl)C(O)[OH:34]>O>[OH:34][N:1]=[CH:2][C:4]([NH:26][C:25]1[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=1[I:23])=[O:5]

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 2707Chloral HydrateHCID 7054IsatinHCID 119952-IodoanilineHCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochloride

Produkt 1

HCID 63998232-(Hydroxyimino)-N-(2-iodophenyl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

Intermediate 5 was prepared according to the method described by Yang et al. (J. Am. Chem. Soc., 1996, 118, 9557), and the cyclization to the isatin was carried out as described by Marvel and Hiers (Org. Synth. Coll. Vol. I, 327). Hydroxylamine hydrochloride (11.4 g, 0.165 mol) and sodium sulfate (52 g, 0.366 mol) were placed in a 1 L round-bottomed flask, and 310 mL water, 16 mL 2 M aqueous hydrochloric acid and 2-iodoaniline (Aldrich, 10 g, 46 mmol) were added. Chloral hydrate (9.1 g, 55 mmol) was then added, and the mixture was heated at 55° C. overnight, with stirring. After cooling to room temperature, the slightly lumpy precipitate was collected by filtration, washing once with water, and dried under vacuum to yield isonitroso intermediate 5 as a beige solid (11.0 g, 83% yield): 1H NMR (400 MHz, DMSO-D6) δ ppm 6.99 (t, J=7.71 Hz, 1H) 7.41 (t, 1H) 7.63 (s, 1H) 7.76 (dd, J=8.08, 1.26 Hz, 1H) 7.90 (dd, J=7.83, 1.26 Hz, 1H) 9.38 (s, 1H) 12.42 (s, 1H).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. filtrationthe slightly lumpy precipitate was collected by filtration
  3. washwashing once with water
  4. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-9193b632ae6449f596c9c3de891c6b02
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07465799B2

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