Hydroxyamine hydrochloride → HCID 178492422, Verbindung

HRID 2278771Notizen

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-d5e437c024b34e8192fa8a2cf5824599
Quelldatensatz: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09133179B2

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