ChemicalBook CAS DataBase List 2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)Methyl)benzonitrile

2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)Methyl)benzonitrile synthesis

5synthesis methods

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

763114-25-6 Synthesis

2-Fluoro-5-((3-oxoisobenzofuran-1(3H)-ylidene)methyl)benzonitrile

763114-25-6
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2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)Methyl)benzonitrile

1021298-68-9
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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

218301-22-5 Synthesis