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

HRID 2375514ノート

反応式

HRID 2375514 の反応式
[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]

参加物

8

反応物 6

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
55 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-9193b632ae6449f596c9c3de891c6b02
出典データセット
uspto-grants-2008_12
特許番号
US07465799B2

反応ノート

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