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

HRID 241486노트

반응식

HRID 241486 반응식
[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]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 10638Luminol

생성물 1

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

시약·촉매·용매 1

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

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-1fe4a8b7ba31481dbb6c6ea70e14ba5d
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08652442B2

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