N,N-dimethyl-5-nitropyridin-2-amine → (6-Dimethylamino-3-nitro-2-pyridyl)acetonitrile

HRID 728765

Reaktionsgleichung

CC(C)([O-])C.[K+].ClC1C=CC(O[CH2:13][C:14]#[N:15])=CC=1.[CH3:18][N:19]([CH3:29])[C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][N:21]=1>CN(C)C=O>[CH3:18][N:19]([CH3:29])[C:20]1[N:21]=[C:22]([CH2:13][C:14]#[N:15])[C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=1

Komponenten

Reaktionsbedingungen

Temperatur: -10 °C

Versuchsvorschrift

To a stirred solution of potassium tert-butoxide (12.34 g, 110 mmol, 2.2 eq) in anhydrous dimethylformamide (100 mL) at -10° C. was added dropwise a solution of (4-chlorophenoxy)acetonitrile (9.22 g, 55 mmol, 1.1eq) and 2-dimethylamino-5-nitropyridine (Pfaltz and Bauer, Inc., 8.36 g, 50.0 mmol) in anhydrous dimethylformamide (50 mL). The resultant deep purple-colored solution was stirred at -10° C. under nitrogen for 1hour. Then an aqueous 5% HCL solution (85 mL) added dropwise to the reaction solution at 0° C., and the precipitated solid was filteredand dried to yield Compound 5c (8.60 g, 41.7 mmol, 83%) as a yellow solid: mp, 156.0-158.0° C.; IR (KBr) 2240, 1600, 1580, 1530, 1485, 1420, 1385, 1335 cm-1 ; 1H NMR (CDCl3) δ 8.25 (d, J=9.0 Hz, 1H), 6.45 (d, J=9.6 Hz, 1H), 4.38 (s, 2H), 3.25 (br s, 6H); LRMS (m/z,relative intensity) 207 (13), 206 (M+, 100), 191 (54), 189 (26), 177 (88), 160 (35), 159 (22), 145 (94), 134 (30), 131 (24), 119 (29), 118 (59), 93 (27). Anal. calcd. for C9H10N4O2 : C, 52,42; H, 4.89; N, 27.17; found: C, 52.19; H, 4.93; N, 26.93.

Aufarbeitung

customthe precipitated solid was filteredand dried

Quellen und Nachweise

ORD-Eintrag: ord-b792ac15e8ec4c3fa77353c9b02b3dd0
Quelldatensatz: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05051412

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