HCID 14773871, compound → HCID 13897640, compound

HRID 329907Notes

Reaction equation

HRID 329907 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:20][OH:21])=[C:13]2[C:18]=1[N+:17]([O-:19])=[CH:16][CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH2:1]([O:8][C:9]1[C:18]2[N+:17]([O-:19])=[CH:16][CH:15]=[CH:14][C:13]=2[C:12]([CH:20]=[O:21])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14773871HCID 14773871, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 13897640HCID 13897640, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-(Benzyloxy)-5-(hydroxymethyl)quinoline N-oxide (3) (0.5 g, 1.78 mmol) was added to a solution of pyridinium chlorochromate (0.42 g, 1.95 mmol) in methylene chloride (10 ml) and the solution was stirred for 1 h, then TLC indicated that the reaction was completed. The solution was then washed with water, dried over Na2SO4, and evaporated. The residue was passed through a short silica gel column using dichloromethane-methanol mixture (100:3) to elute the product. Evaporation gave a yellow solid (4) (0.27 g, 55%): mp 118°-121° C.; Rf 0.64 (chloroform-methanol, 9:1).

Workup

  1. washThe solution was then washed with water
  2. dry with materialdried over Na2SO4
  3. customevaporated
  4. washto elute the product
  5. customEvaporation

Sources & evidence

ORD record
ord-30acf85efdc74747b634cb6e995cdfd5
Source dataset
uspto-grants-1990_01
Patent number
US04894219

Reaction notes

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