m-Chloroperbenzoic acid → HCID 18783935, compound

HRID 1108645Notes

Reaction equation

HRID 1108645 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:25]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[CH:17][C:16]=2[N:15]=[CH:14]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:34])C=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:25]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N+:18]([O-:34])=[CH:17][C:16]=2[N:15]=[CH:14]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 22479013HCID 22479013, compound

Product 1

HCID 18783935HCID 18783935, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

19.47 g (57.19 mmol) of 1-[4-(tert-Butoxycarbonylamino)butyl]-1H-imidazo[4,5-c]quinoline was dissolved in 500 ml of methylene chloride and 15.51 g (62.91 mmol) of 70% m-chloroperbenzoic acid was added thereto. The resulting mixture was stirred overnight at room temperature. A sodium hydrogencarbonate aqueous solution was added to the reaction mixture and the reaction mixture was extracted twice with chloroform. The organic phase was washed with brine and dried (Na2SO4). The solvent was distilled off under reduced pressure and the residue was purified by aluminum column chromatography (chloroform:methanol=50:1 to 10:1 (v/v)). Finally, the resulting product was triturated with diethyl ether and collected by filtration to obtain 15.88 g (44.55 mmol) of 1-[4-(tert-butoxycarbonylamino)butyl]-1H-imidazo[4,5-c]quinoline-5-oxide shown below as yellowish white powder. ##STR54## Its spectroscopic data are as follows: IR (KBr) cm-1 : 3280, 2970, 1710, 1540, 1365, 1250, 1170, 1140, 850, 760, 630.

Workup

  1. extractionthe reaction mixture was extracted twice with chloroform
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by aluminum column chromatography (chloroform:methanol=50:1 to 10:1 (v/v))
  6. customFinally, the resulting product was triturated with diethyl ether
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-3faaaf6ec7074a0c868d02d667925d8f
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

Loading…