Hydrochloric Acid → HCID 72579135, compound

Participants

Reaction Conditions

Reaction Steps

Intermediate 6 was synthesized according to the procedure described by Yang et al. (J. Am. Chem. Soc., 1996, 118, 9557). Hydroxylamine hydrochloride (7.10 g, 0.102 mol) and sodium sulfate (40 g, 0.28 mol) were taken up in 200 mL water and 10 mL 2 M aqueous hydrochloric acid in a 1 L round-bottomed flask, and 1-acetyl-7-amino-2,3-dihydro-(1H)-indole (5.0 g, 28 mmol) was added. Chloral hydrate (5.63 g, 34.0 mmol) was then added, and the flask covered with a rubber septum and nitrogen balloon and heated at 55° C. overnight. After cooling to room temperature, the isonitrosoacetanilide 6 was collected by filtration and dried under vacuum to give product of sufficient purity that it could be used in the next step (5.74 g, 82% yield): 1H NMR (400 MHz, DMSO-D6) δ 2.30 (s, 3H) 3.07 (t, J=8.0 Hz, 2H) 4.13 (t, J=7.8 Hz, 2H) 7.09 (dd, J=7.3, 1.3 Hz, 1H) 7.14 (t, 1H) 7.48 (s, 1H) 7.73 (d, J=7.8 Hz, 1H) 10.76 (s, 1H) 12.33 (s, 1H).

Provenance & Evidence