4-Methoxybenzoic Acid → HCID 13983416, Verbindung
Reaktionsgleichung
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.[NH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[N:16][C:17]([C:23]#[N:24])=[CH:18][CH:19]=2)[N:14]=1>>[C:23]([C:17]1[N:16]=[C:15]2[C:20]([CH:21]=[CH:22][C:13]([NH:12][C:7](=[O:9])[C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)=[N:14]2)=[CH:19][CH:18]=1)#[N:24]Komponenten
3
Versuchsvorschrift
The procedure is similar to that described in Example 1, but starting with 4-methoxybenzoic acid (8.2 g), N,N'-carbonyldiimidazole (8.7 g) and 2-amino-7-cyano-1,8-naphthyridine (6.9 g), and heating for 4 hours under reflux. The insoluble product is separated by filtration and the filtrate is poured into water (1000 cc). The resulting precipitate is filtered off, washed with water (3×75 cc) and dried in the air. The solid obtained is purified by flash chromatography (under 30 kPa) on a column 40 mm in diameter containing silica (170 g; 0.04-0.06 mm), eluting with pure methylene chloride and collecting 50-cc fractions. After concentration of fractions 5 to 27 to dryness at 40° C. under reduced pressure (4 kPa), the product obtained is purified by recrystallization in dioxane (160 cc). N-(7-Cyano-1,8-naphthyridin-2-yl)-4-methoxybenzamide (1.4 g), m.p. 283° C., is thereby obtained.