Nitric Acid → HCID 21890031, compound

HRID 721629Notes

Reaction equation

HRID 721629 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:36]=[CH:35][C:9]([O:10][CH2:11][CH2:12][S:13][C:14]2[CH:34]=[CH:33][C:17]([O:18][C:19]3[C:28]4[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=4)[N:22]=[CH:21][CH:20]=3)=[CH:16][CH:15]=2)=[CH:8][CH:7]=1.C(=O)([O-])[OH:38].[Na+]>>[CH3:30][O:29][C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][C:25]=1[O:31][CH3:32])[N:22]=[CH:21][CH:20]=[C:19]2[O:18][C:17]1[CH:33]=[CH:34][C:14]([S:13]([CH2:12][CH2:11][O:10][C:9]2[CH:8]=[CH:7][C:6]([F:5])=[CH:36][C:35]=2[N+:1]([O-:4])=[O:2])=[O:38])=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 21890606HCID 21890606, compound

Product 1

HCID 21890031HCID 21890031, compoundYield 58%

Conditions

Temperature
0 °C

Procedure

Nitric acid (0.5 ml) was added to 4-(4-{[2-(4-Fluorophenoxy)ethyl]sulfanyl}phenoxy)-6,7-dimethoxyquinoline (20 mg), and the mixture was stirred at 0° C. for 30 min. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with chloroform, followed by washing with saturated brine. The extract was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by thin-layer chromatography using chloroform/methanol for development to give the title compound (13 mg, yield 58%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washby washing with saturated brine
  3. dry with materialThe extract was then dried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. customThe residue was purified by thin-layer chromatography

Sources & evidence

ORD record
ord-ef25efae34a04d2f831885e96ab65b03
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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