Nitric Acid → HCID 58739022, compound

HRID 721630Notes

Reaction equation

HRID 721630 reaction equation
[N+]([O-])(O)=O.[Cl:5][C:6]1[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:7]=1[O:8][CH2:9][CH2:10][S:11][C:12]1[CH:32]=[CH:31][C:15]([O:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:29][CH3:30])=[C:24]([O:27][CH3:28])[CH:25]=3)[N:20]=[CH:19][CH:18]=2)=[CH:14][CH:13]=1.C(=O)([O-])[OH:39].[Na+]>>[Cl:5][C:6]1[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:7]=1[O:8][CH2:9][CH2:10][S:11]([C:12]1[CH:32]=[CH:31][C:15]([O:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:29][CH3:30])=[C:24]([O:27][CH3:28])[CH:25]=3)[N:20]=[CH:19][CH:18]=2)=[CH:14][CH:13]=1)=[O:39]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 21890246HCID 21890246, compound

Product 1

HCID 58739022HCID 58739022, compoundYield 92%

Conditions

Temperature
0 °C

Procedure

Nitric acid (0.5 ml) was added to 4-(4-{[2-(2,4-dichlorophenoxy)ethyl]sulfanyl}phenoxy)-6,7-dimethoxyquinoline (20 mg), and the mixture was stirred at 0° C. for one hr. 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 (19 mg, yield 92%).

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-227e69f111e84dbcabd43883a89ea54e
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

Loading…