Hydrochloric Acid → HCID 72579135, compound

HRID 2375555Notes

Reaction equation

Cl.[NH2:2][OH:3].S([O-])([O-])(=O)=O.[Na+].[Na+].Cl.[C:12]([N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[NH2:24])[CH2:17][CH2:16]1)(=[O:14])[CH3:13].Cl[C:26](Cl)(Cl)[CH:27]([OH:29])O>O>[C:12]([N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[NH:24][C:27](=[O:29])[CH:26]=[N:2][OH:3])[CH2:17][CH2:16]1)(=[O:14])[CH3:13]

Participants

Conditions

Temperature: 55 °C

Procedure

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).

Workup

temperatureAfter cooling to room temperature
filtrationthe isonitrosoacetanilide 6 was collected by filtration
customdried under vacuum
customto give product of sufficient purity that it

Sources & evidence

ORD record: ord-0bbb3b623f7a4281836086a0041966a3
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465798B2

Reaction notes

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