تفاعل #3254

ord-ce23a4c71bca4f4ba6dee847e17f8171

معادلة التفاعل

CN(C)CCNc1nc2cc(O)ccc2c2c1C(=O)c1ccccc1-2
6-(((dimethylamino)ethyl)amino)-3-hydroxy-7H-indeno[2,1-c]quinoline-7-on
O=S(=O)(O)O
sulfuric acid
O=[N+]([O-])O
nitric acid
CN(C)CCNc1nc2c([N+](=O)[O-])c(O)ccc2c2c1C(=O)c1ccccc1-2
title compound
المردود 52.9%
CN(C)CCNc1nc2c([N+](=O)[O-])c(O)ccc2c2c1C(=O)c1ccccc1-2
6-(((dimethylamino)ethyl)amino)-3-hydroxy-4-nitro-7H-indeno[2,1-c]quinoline-7-on
المردود 52.9%

ظروف التفاعل

درجة الحرارة
5°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىa crystal precipitated
  2. 2
    ترشيحwas collected by filtration
  3. 3
    أخرىThe crystal obtained
  4. 4
    أخرىwas purified by silica gel column chromatography (eluent
  5. 5
    أخرىa lower layer of chloroform:methanol:water=9:3:1(v/v/v)) and crystallized from ethanol-diethylether

الإجراء التجريبي

A mixture of 6-(((dimethylamino)ethyl)amino)-3-hydroxy-7H-indeno[2,1-c]quinoline-7-on obtained in example 3 (100 mg, 0.3 mmol), conc. sulfuric acid (1 ml) and nitric acid (1 ml) was stirred at 5° C. for 2 hours. The reaction mixture was poured into ice water, and a crystal precipitated was collected by filtration. The crystal obtained was purified by silica gel column chromatography (eluent; a lower layer of chloroform:methanol:water=9:3:1(v/v/v)) and crystallized from ethanol-diethylether to give 60 mg (yield: 52.9%) of title compound. The physicochemical properties thereof are shown in table 1.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05733918uspto-grants-1998_03