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Sodium Sulfate → 3-Nitro-7-(5-methyl-2-phenyl-4-oxazolylmethoxy)quinoline

HRID 1938339
Notes
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Reaction equation

HRID 1938339 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([OH:14])[CH:8]=2)([O-:3])=[O:2].[H-].[Na+].Cl[CH2:18][C:19]1[N:20]=[C:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:22][C:23]=1[CH3:24].S([O-])([O-])(=O)=O.[Na+].[Na+]>CN(C=O)C.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([O:14][CH2:18][C:19]1[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:23]=1[CH3:24])[CH:8]=2)([O-:3])=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 24436Sodium SulfateHCID 24758Sodium hydrideHCID 97942894-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazoleHCID 1357342933-Nitroquinolin-7-ol

Product 1

HCID 214693263-Nitro-7-(5-methyl-2-phenyl-4-oxazolylmethoxy)quinolineYield 48.3%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

In DMF (9 mL) was dissolved 3-nitro-7-hydroxyquinoline (800 mg, 4.24 mmol.). Sodium hydride (168 mg, 4.24 mmol.) and 4-chloromethyl-5-methyl-2-phenyloxazole (880 mg, 4.24 mmol.) were added to the resulting solution under chilling with ice. The mixture was stirred overnight at 50°-60° C. After the completion of reaction was confirmed, ethyl acetate and aqueous sodium sulfate were added. The ethyl acetate portion was recovered, washed with water, and dried over sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1), to give 740 mg of the desired compound as a yellow-white crystalline product (yield 48%).

Workup

  1. temperatureunder chilling with ice
  2. customAfter the completion of reaction
  3. customThe ethyl acetate portion was recovered
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-44e7b8406f1748dfbeaf10200177e1ae
Source dataset
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05693651

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes