N-[3-cyano-4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-quinolinyl]acetamide → 7-Amino-4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-3-quinolinecarbonitrile

HRID 396188

Reaktionsgleichung

[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[NH:13][C:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([Cl:22])=[CH:16][C:15]=1[Cl:23])=[CH:10][C:9]([O:24][CH3:25])=[C:8]([NH:26]C(=O)C)[CH:7]=2)#[N:2]>Cl>[NH2:26][C:8]1[CH:7]=[C:6]2[C:11]([C:12]([NH:13][C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([Cl:22])=[CH:16][C:15]=3[Cl:23])=[C:3]([C:1]#[N:2])[CH:4]=[N:5]2)=[CH:10][C:9]=1[O:24][CH3:25]

Komponenten

Reaktionsbedingungen

Temperatur: 65 °C

Versuchsvorschrift

An amount of 5 g (0.012 mol) of N-[3-cyano-4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-quinolinyl]acetamide was stirred in 37% hydrochloric acid (500 mL), and heated at 65° C. for 1 hour. The mixture was evaporated to a slurry, stirred in saturated sodium bicarbonate solution, and extracted with ethyl acetate. The organic phase was dried over sodium sulfate, filtered through a pad of silica gel, and evaporated to dryness to give a tan solid (1.9 g, 42% yield), mp 265° C. decomp.; 1H NMR (DMSO-d6) δ 9.29 (s, 1H), 8.27 (s, 1H), 7.70 (s, 1H), 7.66 (s, 1H), 7.23 (s, 1H), 6.98 (s, 1H), 5.93 (s, 2H), 3.96 (s, 3H), 3.84 (s, 3H); MS (ES) m/z 389.2 (M+1). Analysis for C18H14Cl2N4O2: Found: C, 55.80; H, 3.78; N, 14.67. Calcd: C, 55.54; H, 3.63; N, 14.39.

Aufarbeitung

customThe mixture was evaporated to a slurry
extractionextracted with ethyl acetate
dry with materialThe organic phase was dried over sodium sulfate
filtrationfiltered through a pad of silica gel
customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag: ord-08846a2e24c9410785d710585d4484a0
Quelldatensatz: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06608048B2

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