Pyridine → 2-Chloro-N-(1,4-dioxo-1,2,3,4-tetrahydrophthalazine-5-yl)acetamide

HRID 241486Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 241486
[CH:1]1[CH:6]=[C:5]([NH2:7])[C:4]2[C:8]([NH:10][NH:11][C:12](=[O:13])[C:3]=2[CH:2]=1)=[O:9].[Cl:14][CH2:15][C:16](Cl)=[O:17].N1C=CC=CC=1>CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>[Cl:14][CH2:15][C:16]([NH:7][C:5]1[CH:6]=[CH:1][CH:2]=[C:3]2[C:4]=1[C:8](=[O:9])[NH:10][NH:11][C:12]2=[O:13])=[O:17]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 10638Luminol

Produkt 1

HCID 543576732-Chloro-N-(1,4-dioxo-1,2,3,4-tetrahydrophthalazine-5-yl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterLösungsmittel

Versuchsvorschrift

Luminol (1.55 g; 8.75 mmol) was reacted with 2-chloro-acetylchloride (1.24 g; 10.99 mmol), in the presence of pyridine (1.07 g, 13.6 mmol) in acetic:acid (45 ml). Contents were stirred and refluxed for 1 h, allowed to cool to RT, and transferred to a refrigerator for precipitation of the product to obtain 2-Chloro-N-(1,4-dioxo-1,2,3,4-tetrahydrophthalazine-5-yl)acetamide. Thereafter, acetic acid (20 ml) was added to the cold precipitates prior to filtration (for uniform transfer into the filtration unit). Finally, precipitates were filtered, washed with methylene chloride (three times) and dried under vacuum to yield 2-Chloro-N-(1,4-dioxo-1,2,3,4-tetrahydrophthalazine-5-yl)acetamide (1.6 g; 6324 mmol; 72.2%). 1H NMR (300 MHz, DMSO-d6) δ: 8.82-8.87 (t, 1H), 7.71-7.89 (dd, 1H), 7.61-7.69 (dd, 1H), 4.34 (s, 2H), 2.16 (s, 3H, Methyl for Acetic Acid); ESMS: Calcd for C10H8ClN3O3: 253.0, Found, 253.8.

Aufarbeitung

  1. temperaturerefluxed for 1 h
  2. customtransferred to a refrigerator for precipitation of the product

Quellen und Nachweise

ORD-Eintrag
ord-1fe4a8b7ba31481dbb6c6ea70e14ba5d
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08652442B2

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