2-Bromophenylhydrazine hydrochloride → HCID 67238175, Verbindung

HRID 1623056

Reaktionsgleichung

[ClH:1].[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9]N.O=[C:12]1[CH2:18][CH:17]2[N:19](C(OC(C)(C)C)=O)[CH:14]([CH2:15][CH2:16]2)[CH2:13]1>Cl.C(O)(=O)C>[ClH:1].[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[NH:9][C:12]1[CH2:13][CH:14]3[NH:19][CH:17]([C:18]2=1)[CH2:16][CH2:15]3

Komponenten

Reaktionsbedingungen

Temperatur: 22.5 °C

Versuchsvorschrift

A mixture of 2-bromophenylhydrazine hydrochloride (4.44 g, 19.81 mmol, Aldrich) and t-butyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate (4.48 g, 19.89 mmol, Chem-Impex) in 1 M HCl/acetic acid was stirred at 20-25° C. for 20 hours, and then heated at 65-70° C. for 48 hours. The mixture was cooled to room temperature and concentrated under vacuum. The residue was heated to boiling in absolute ethanol (25 mL) and the suspension was stirred at room temperature for 2 hours, then filtered. The solid was washed with cold ethanol and dried under vacuum to provide the title compound: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.74-1.86 (m, 1H), 2.07 (t, J=9.7 Hz, 1H), 2.15-2.32 (m, 2H), 2.88 (d, J=17.4 Hz, 1H), 3.35-3.49 (m, 1H), 4.41 (s, 1H), 5.16 (d, J=4.4 Hz, 1H), 6.98 (t, J=7.7 Hz, 1H), 7.25-7.37 (m, 1H), 7.58 (d, J=7.9 Hz, 1H), 8.63-9.49 (m, 1H), 11.37 (s, 1H); MS (DCI/NH3) m/z 277/279 (M+H)+.

Aufarbeitung

temperatureheated at 65-70° C. for 48 hours
temperatureThe mixture was cooled to room temperature
concentrationconcentrated under vacuum
temperatureThe residue was heated
stirringthe suspension was stirred at room temperature for 2 hours
filtrationfiltered
washThe solid was washed with cold ethanol
customdried under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-6cd066fcf4e444b78ea59c84c21acf22
Quelldatensatz: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08778959B2

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