HCID 18348926, compound → HCID 18349091, compound

HRID 2268571Notes

Reaction equation

HRID 2268571 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:18][OH:19])[CH:5]=[C:6]([O:8][CH2:9][CH2:10][NH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH:7]=1>O1CCOCC1.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([O:8][CH2:9][CH2:10][NH:11][C:12]2[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=2)[CH:7]=1)[CH:18]=[O:19]

Participants

4

Reactant 1

HCID 18348926HCID 18348926, compound

Product 1

HCID 18349091HCID 18349091, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A suspension of {3-bromo-5-[2-(pyridin-4-ylamino)-ethoxy]-phenyl}-methanol (1.4 g) and manganese dioxide (3.2 g) in 1,4-dioxan (50 ml) was heated to reflux with stirring under an atmosphere of dry nitrogen for 8 h. After cooling to room temperature the mixture was stirred at room temperature for 16 h, and then filtered through Harborlite® and the pad washed with hot methanol. The combined filtrates were evaporated to dryness under reduced pressure to give the title compound as an off-white solid (1.2 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. stirringwas stirred at room temperature for 16 h
  4. filtrationfiltered through Harborlite®
  5. washthe pad washed with hot methanol
  6. customThe combined filtrates were evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-c2d23bda00be40dbbefe323de2748354
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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