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

HRID 2375514Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 55 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-9193b632ae6449f596c9c3de891c6b02
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465799B2

Reaction notes

Loading…