Diethyl Ether → HCID 18349077, compound

HRID 2268566Notes

Reaction equation

HRID 2268566 reaction equation
[CH3:1][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.C(OCC)C>O1CCOCC1.[O-2].[O-2].[Mn+4]>[CH3:1][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

5

Reactant 2

HCID 3283Diethyl EtherHCID 18349112HCID 18349112, compound

Product 1

HCID 18349077HCID 18349077, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A suspension of {3-methyl-5-[2-(pyridin-4-ylamino)-ethoxy]-phenyl}-methanol (0.132 g) and manganese dioxide (0.370 g) in 1,4-dioxan (5 ml) was heated to reflux with stirring under an atmosphere of dry nitrogen for 5 h. After cooling to room temperature the mixture was filtered through Harborlite® and the pad washed with 1,4-dioxan and then methanol. The combined filtrates were evaporated to dryness under reduced pressure to give an off-white solid. Trituration with diethyl ether gave, after drying, the title compound as a white powder (0.074 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. filtrationwas filtered through Harborlite®
  4. washthe pad washed with 1,4-dioxan
  5. customThe combined filtrates were evaporated to dryness under reduced pressure
  6. customto give an off-white solid
  7. customafter drying

Sources & evidence

ORD record
ord-36b5cfd194d34360890bc792e4fab679
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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