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2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)Methyl)benzonitrile synthesis
- Product Name:2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)Methyl)benzonitrile
- CAS Number:1021298-68-9
- Molecular formula:C16H10FN3O
- Molecular Weight:279.27
![2-Fluoro-5-((3-oxoisobenzofuran-1(3H)-ylidene)methyl)benzonitrile](/CAS2/GIF/763114-25-6.gif)
763114-25-6
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![2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)Methyl)benzonitrile](/CAS/20150408/GIF/1021298-68-9.gif)
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Yield:-
Reaction Conditions:
Stage #1: 2-fluoro-5-[(3'-oxo-2'-benzofuran-1'-ylidene)methyl]benzonitrilewith hydrazine in tetrahydrofuran at 20; for 2.25 h;
Stage #2: with acetic acid in tetrahydrofuran at 60;
Steps:
4.b
(b) 2-Fluoro-5-[(4-oxo-3, 4-dihydrophthalazin-1-yl)methyl]benzonitrile (ED) 2-Fluoro-5-[(E/Z)-(3-oxo-2-benzofuran-1 (3/-/)-ylidene)methyl]benzonitrile (E)(20g, 75.40 mmol) and tetrahydrofuran (200 ml) were stirred at room temperature under a nitrogen atmosphere for 30 minutes. Hydrazine monohydrate (4.40 ml, 90.53 mmol) was added, followed by a line wash of tetrahydrofuran (4 ml). The reaction mixture was stirred at room temperature for 1 hour 45 minutes. Acetic acid (1.10 ml, 19.20 mmol) was added and the reaction mixture warmed to 600C. The reaction mixture was held at 600C overnight. The reaction mixture was cooled to 50°C and water (200 ml) added dropwise. The temperature was maintained at 45°C throughout the addition. The reaction mixture was cooled to 200C1 filtered, washed with a mixture of water (30 ml) and tetrahydrofuran (30 ml), and then dried in vacuo at up to 4O0C to give the title compound (18.7 g).Mass spectrum: MH+ 2801 H NMR (400MHz. DMSO-d6) δ: 4.38 (s, 2H), 7.46 (t, 1 H), 7.72 (m, 1 H), 7.85 (dt, 1 H), 7.92 (m, 2H), 7.99 (d, 1 H), 8.27 (dd, 1 H), 12.57 (s, 1 H).
References:
WO2008/47082,2008,A2 Location in patent:Page/Page column 28
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218301-22-5
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![2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)Methyl)benzonitrile](/CAS/20150408/GIF/1021298-68-9.gif)
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77771-02-9
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![2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)Methyl)benzonitrile](/CAS/20150408/GIF/1021298-68-9.gif)
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119-67-5
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![2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)Methyl)benzonitrile](/CAS/20150408/GIF/1021298-68-9.gif)
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