Water → HCID 13672383, compound

HRID 542550Notes

Reaction equation

HRID 542550 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N+:12]([O-:19])=[C:11]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]=[O:31])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=[O:34].OS(O)(=O)=O.O=[Cr](=O)=O.S(=O)(=O)(O)O.O>CC(C)=O.[O-2].[O-2].[O-2].[Cr+6]>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N+:12]([O-:19])=[C:11]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:34])=[O:31])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 1118Sulfuric AcidHCID 13672382HCID 13672382, compoundHCID 131709961Jones' reagent

Product 1

HCID 13672383HCID 13672383, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolvent

Procedure

In this example, 5 m moles of 4-benzyloxy-2-(10-formyldecyl) quinoline-N-oxide is dissolved in acetone, and 10 m moles of Jones' reagent prepared from chromium trioxide, sulfuric acid and water is added thereto with ice cooling. The mixture is stirred for 5 minutes. After the reaction, water is added thereto, and the reaction mixture is extracted with chloroform. The extract is dried over anhydrous sodium sulfate, and then the solvent is removed therefrom by distillation. The residue is purified by silica gel column procedure, whereby the captioned compound is obtained as colorless crystals (yield: 31.0%).

Workup

  1. additionis added
  2. additionis added
  3. extractionthe reaction mixture is extracted with chloroform
  4. dry with materialThe extract is dried over anhydrous sodium sulfate
  5. customthe solvent is removed
  6. distillationby distillation
  7. customThe residue is purified by silica gel column procedure, whereby the captioned compound

Sources & evidence

ORD record
ord-d59652a6c5b54ed088660b7b58965d86
Source dataset
uspto-grants-1987_04
Patent number
US04657916

Reaction notes

Loading…