HCID 118232987, Verbindung → 3-(3-chloro-4-methyl-1H-pyrazol-1-yl)pyridine

HRID 1525781Notizen

Reaktionsgleichung

[Cl:1][C:2]1[CH:6]([CH3:7])[CH2:5][N:4]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[N:3]=1>C(#N)C.[O-2].[Mn+4].[O-2]>[Cl:1][C:2]1[C:6]([CH3:7])=[CH:5][N:4]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[N:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 22 °C

Versuchsvorschrift

To a solution of 3-(3-chloro-4-methyl-4,5-dihydro-1H-pyrazol-1-yl)pyridine (1.0 g, 5.0 mol) in acetonitrile (10.0 mL) at 0° C. was added manganese(IV) oxide (1.3 g, 15 mmol) portionwise over 10 minutes. The mixture was slowly warmed to 22° C. over 40 minutes and then heated to 40° C. overnight. After 20 hours, additional manganese(IV) oxide (0.44 g, 5.0 mmol) was added in one portion and the mixture was stirred for 1 hour. The mixture was cooled down and filtered. The filter cake was washed with acetonitrile (3×15 mL). The organic filtrate was dried and concentrated to afford the title compound as a light yellow solid (0.92 g, 95%): 1H NMR (400 MHz, CDCl3) δ 8.90 (dd, J=2.6, 0.8 Hz, 1H), 8.52 (dd, J=4.8, 1.5 Hz, 1H), 7.99 (ddd, J=8.3, 2.7, 1.4 Hz, 1H), 7.74 (q, J=0.9 Hz, 1H), 7.39 (ddd, J=8.3, 4.8, 0.8 Hz, 1H), 2.13 (d, J=0.9 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 147.26, 142.87, 139.53, 135.90, 126.53, 125.69, 123.84, 116.86, 22.47; EIMS m/z 193 ([M]+).

Aufarbeitung

temperatureheated to 40° C. overnight
temperatureThe mixture was cooled down
filtrationfiltered
washThe filter cake was washed with acetonitrile (3×15 mL)
customThe organic filtrate was dried
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-9b5fe8c559d0493781d49805a98fdb4d
Quelldatensatz: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09085552B1

Notizen zur Reaktion

Wird geladen…