Hydroxyamine hydrochloride → HCID 178492422, Verbindung

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Reaktionsgleichung

[CH:1]1([C:6]2[CH:7]=[C:8]([CH:11]=[C:12]([O:14][CH3:15])[N:13]=2)[C:9]#[N:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH2:17][OH:18].C([O-])(O)=O.[Na+]>CO>[CH:1]1([C:6]2[CH:7]=[C:8]([CH:11]=[C:12]([O:14][CH3:15])[N:13]=2)[C:9]([NH:17][OH:18])=[NH:10])[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To a solution of 2-cyclopentyl-6-methoxy-isonicotinonitrile (2.09 g, 10.3 mmol) in methanol (100 mL), hydroxylamine hydrochloride (2.15 g, 31.0 mmol) and NaHCO3 (3.04 g, 36.2 mmol) are added. The mixture is stirred at 60° C. for 18 h before it is filtered and the filtrate is concentrated. The residue is dissolved in EA (300 mL) and washed with water (30 mL). The washings are extracted back with EA (4×100 mL) and DCM (4×100 mL). The combined org. extracts are dried over MgSO4, filtered, concentrated and dried under HV to give the title compound (2.74 g) as a white solid; LC-MS**: tR=0.47 min, [M+1]+=236.24; 1H NMR (D6-DMSO): δ 1.61-1.82 (m, 6H), 1.92-2.01 (m, 2H), 3.04-3.13 (m, 1H), 3.84 (s, 3H), 5.90 (s, 2H), 6.86 (s, 1H), 7.13 (s, 1H), 9.91 (s, 1H).

Aufarbeitung

filtrationis filtered
concentrationthe filtrate is concentrated
dissolutionThe residue is dissolved in EA (300 mL)
washwashed with water (30 mL)
extractionThe washings are extracted back with EA (4×100 mL) and DCM (4×100 mL)
dry with materialextracts are dried over MgSO4
filtrationfiltered
concentrationconcentrated
customdried under HV

Quellen und Nachweise

ORD-Eintrag: ord-2286104a866b44e6a54b8c9fcc25bd15
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08658675B2

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