Nitric Acid → 6-(((dimethylamino)ethyl)amino)-3-hydroxy-4-nitro-7H-indeno[2,1-c]quinoline-7-on

HRID 3158Notes

Reaction equation

HRID 3158 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][NH:6][C:7]1[C:16]2[C:17](=[O:24])[C:18]3[C:23]([C:15]=2[C:14]2[C:9](=[CH:10][C:11]([OH:25])=[CH:12][CH:13]=2)[N:8]=1)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH3:3].S(=O)(=O)(O)O.[N+:31]([O-])([OH:33])=[O:32]>>[CH3:3][N:2]([CH2:4][CH2:5][NH:6][C:7]1[C:16]2[C:17](=[O:24])[C:18]3[C:23]([C:15]=2[C:14]2[C:9](=[C:10]([N+:31]([O-:33])=[O:32])[C:11]([OH:25])=[CH:12][CH:13]=2)[N:8]=1)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH3:1]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 135413533TAS-103 free base

Product 1

HCID 1359669146-(((dimethylamino)ethyl)amino)-3-hydroxy-4-nitro-7H-indeno[2,1-c]quinoline-7-onYield 52.9%

Conditions

Temperature
5 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-ce23a4c71bca4f4ba6dee847e17f8171
Source dataset
uspto-grants-1998_03
Patent number
US05733918

Reaction notes

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